ChemicalBook CAS DataBase List GS 9451

GS 9451 synthesis

13synthesis methods

Product Name:GS 9451
CAS Number:1098189-15-1
Molecular formula:C45H60ClN7O9S
Molecular Weight:910.53

Cyclopropanecarboxyl?ic acid, N-?[[(1α,?3β,?5α)?-?bicyclo[3.1.0]?hex-?3-?yloxy]?carbonyl]?-?3-?methyl-?L-?valyl-?(4R)?-?4-?[[8-?chloro-?2-?[2-?[(1-?methylethyl)?amino]?-?4-?thiazolyl]?-?7-?[2-?(4-?morpholinyl)?ethoxy]?-?4-?quinolinyl]?oxy]?-?L-?prolyl-?1-?amino-?2-?ethyl-?, methyl ester, (1R,?2R)?-

1098189-14-0
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1098189-15-1
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Yield:1098189-15-1 93%

Reaction Conditions:

with water;lithium hydroxide in tetrahydrofuran;methanol at 20; for 20 h;

Steps:

3 Example 3: Preparation of Compound 3
Example 3: Preparation of Compound 3 Compound 315 (12 g, 13 mmol) was dissolved in THF (200 ml), LiOH (11g, 260 mmol) in H₂0 (200 ml) was added, followed by MeOH (200 ml). The mixture was kept stirring at room temperature for 20 hours. Upon completion of the reaction, 4 N HCI in H₂0 was added to adjust pH to 7 at 0 °C. The mixture was extracted with EtOAc (2 x 400 ml). The combined organic layer was washed with brine, dried (Na₂S0₄) and concentrated in vacuo to give compound 3 as a yellow solid (11 g, 93%). LC/MS = 911.52(M⁺+1 ). ¹H NMR (300MHz, CD₃OD) 57.95 (d, 1H), 7.90 (s, 1H), 7.48 (s, 1H), 7.31 (d, 1H), 5.42 (s, 1H), 4.37 (dd, 1H), 4.20 (m, 2H), 3.83-3.56 (m, 7H), 3.50 (m, 2H), 3.39 (m, 2H), 2.45 (m, 1H), 2.27(m, 1H), 1.62 (m, 2H), 1.50 (m, 1H), 1.33 (m, 2H), 1.18 (m, 1H), 1.05 (m, 8H), 0.90 (m, 3H), 0.76 (m, 11H), 0.14-0.04 (m, 2H)

References:

GILEAD SCIENCES, INC.;RAY, Adrian S.;WATKINS, William J.;LINK, John O.;OLDACH, David W.;DELANEY, IV, William E. WO2013/40492, 2013, A2 Location in patent:Page/Page column 67

FullText

Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)-

923289-36-5
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1098189-15-1
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References

Ethanone, 1-?(2-?amino-?3-?chloro-?4-?hydroxyphenyl)?-

1098189-00-4
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1098189-15-1
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References

Ethanone, 1-?[2-?amino-?3-?chloro-?4-?(2,?2-?dimethoxyethoxy)?phenyl]?-

1098189-01-5
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1098189-15-1
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References

4-?Quinolinol, 8-?chloro-?7-?(2,?2-?dimethoxyethoxy)?-?2-?[2-?[(1-?methylethyl)?amino]?-?4-?thiazolyl]?-

1098189-06-0
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1098189-15-1
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References