ChemicalBook CAS DataBase List JAK3-IN-6

JAK3-IN-6 synthesis

4synthesis methods

Product Name:JAK3-IN-6
CAS Number:1443235-95-7
Molecular formula:C19H18N4O3
Molecular Weight:350.37

7H-Pyrrolo[2,3-d]pyrimidine-5-carboxylic acid, 4-(3-aminophenyl)-, ethyl ester

1443234-84-1
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920-46-7
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1443235-95-7
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Yield:-

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in tetrahydrofuran at 15 - 25; for 1 h;Inert atmosphere;

Steps:

4-1 Ethyl-4- ( 3 - [(2-methylacryloyl)amino]phenyl } -7H-pyrrolo [2,3 -ci]pyrimidine-5- carboxylate (4-1)

To a solution of ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-iflpyrimidine-5- carboxylate (50 mg, 0.18 mmol) and DIPEA (93 μ,, 0.53 mmol) in THF (1.8 mL) at room temperature was added methacryloyl chloride (27.8 mg, 0.266 mmol) and the solution stirred for 1 hour. The reaction was quenched with ethanol (0.1 mL). The desired product was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The combined fractions with the desired product were concentrated until only the water layer remained. The water layer was neutralized with 2M aqueous potassium bicarbonate and the mixture was extracted with ethyl acetate (x5). The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure to give ethyl 4-{3-[(2-methylacryloyl)amino]phenyl}-7H- pyrrolo[2,3-^pyrimidine-5-carboxylate. LRMS (ESI) calc'd for Ci₉H₁₉N₄0₃ [M+H]⁺: 351, found 351. NMR (600 MHz, DMSO-D₆) δ 13.0 (s, 1H), 9.91 (s, 1H), 8.91 (s, 1H), 8.30 (s, 1H), 8.05 (s, 1H), 7.84 (d, 1H, J = 7.04 Hz), 7.40 (t, 1H, J= 7.63 Hz), 7.32 (d, 1H, J = 7.04 Hz), 5.82 (s, 1H), 5.53 (s, 1H), 3.86 (q, 2H, J = 7.04 Hz), 1.95 (s, 3H), 0.85 (t, 3H, J= 7.04 Hz).

References:

WO2013/85802,2013,A1 Location in patent:Page/Page column 82

22276-95-5 Synthesis

5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

22276-95-5
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References

ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

144927-57-1
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1443235-95-7
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References

3680-69-1 Synthesis

3680-69-1
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References