ChemicalBook CAS DataBase List CC-90001

CC-90001 synthesis

10synthesis methods

Product Name:CC-90001
CAS Number:1403859-14-2
Molecular formula:C16H27N5O2
Molecular Weight:321.42

2,4-di-chloropyrimidine 5-carboxylic acid amide

1240390-28-6
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$21.00/250mg

(1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride

1403864-98-1
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1403859-14-2
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Yield: 86%

Reaction Conditions:

with potassium carbonate in tetrahydrofuran;water at 0 - 25; for 17 h;Large scale;

Steps:

1 Example 1: 2-(tert-Butylamino)-4-{[(lR,3R,4R)-3-hydroxy-4- methylcyclohexyl]amino}pyrimidine-5-carboxamide
Example 1: 2-(tert-Butylamino)-4-{[(lR,3R,4R)-3-hydroxy-4- methylcyclohexyl]amino}pyrimidine-5-carboxamide [00443] 2-Chloro-4-{[(lR,3R,4R)-3-hydroxy-4-methylcyclohexyl]amino}pyrimidine- 5-carboxamide: To a reactor was added (lR,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride (16.0 kg), 2,4-dichloropyrimidine-5-carboxamide (19.0 kg), K₂CO₃ (14.9 kg) and THF (160 L) at 25 °C. The batch was cooled to 0 °C, and water (160 L) was added. The batch was stirred for an additional 1 h at 0 °C, warmed to 25 °C and held for 16 h. Water (288 L) was added to the batch while keeping the batch at 25 °C, and the batch was cooled to 15 °C and agitated for an additional 4 hs. The batch was filtered, rinsed twice with water (2X80 L), and dried in a vacuum oven at 40 °C with nitrogen bleed for 24 h to give 2-chloro-4-{[(lR,3R,4R)-3- hydroxy-4-methylcyclohexyl] amino }pyrimidine-5-carboxamide as white powder (23.3 kg, 86% yield). 1H NMR (DMSO-d₆) δ 0.93 (d, J = 5.7 Hz, 3H), 0.97- 1.29 (m, 4H), 1.63- 1.68 (m, 1H), 1.75- 1.88 (m, 1H), 2.09-2.13 (m, 1H), 3.00-3.08 (m, 1H), 3.80-3.95 (m, 1H), 4.65 (d, J = 5.1 Hz, 1H), 7.69 (br. s., 1H), 8.20 (br. s., 1H), 8.53 (s, 1H), 9.22 (d, J = 7.5 Hz, 1H).

References:

SIGNAL PHARMACEUTICALS, LLC;FERRETTI, Antonio Christian;MAN, Hon-Wah;MUSLEHIDDINOGLU, Jale;XU, Jean;YONG, Kelvin Hin-yeong;BEAUCHAMPS, Marie Georges;KOTHARE, Mohit Atul;ZHOU, Nanfei;BOERSEN, Nathan Andrew;LI, Ying;HILGRAF, Robert;NAGY, Mark A.;ZOU, Daozhong;HUANG, Lianfeng WO2015/116755, 2015, A2 Location in patent:Paragraph 00443

2-(tert-butylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide

1403865-02-0
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1403864-98-1
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1403859-14-2
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References

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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1403859-14-2
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References

2-(tert-butylamino)-4-(methylthio)pyrimidine-5-carbonitrile

1403865-00-8
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1403859-14-2
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2-(tert-butylamino)-4-(methylthio)pyrimidine-5-carboxamide

1403865-01-9
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1403859-14-2
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References