Methyl 3-mercaptopropionate → Methyl 3-(5-phenoxy-6-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate

HRID 911853Notes

Reaction equation

HRID 911853 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([NH:8][C:9]2[S:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:6][CH:7]=1.[SH:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(N(C(C)C)C(C)C)C>>[O:18]([C:4]1[CH:3]=[C:2]([S:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:7]=[N:6][C:5]=1[NH:8][C:9]1[S:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[CH:13][N:12]=2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 18050Methyl 3-mercaptopropionateHCID 81531DiisopropylethylamineHCID 57742902N-(5-Bromo-3-phenoxypyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

Product 1

HCID 57742885Methyl 3-(5-phenoxy-6-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoateYield 75%

Procedure

Prepared according to the method of Example 13 from N-(5-bromo-3-phenoxypyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine, methyl 3-mercaptopropanoate and N-ethyl-N-isopropylpropan-2-amine in 75% yield. 1H NMR (d6-DMSO) δ 2.59 (t, 2H), 3.09 (t, 2H), 3.56 (s, 3H), 7.12 (d, 2H), 7.20 (t, 1H), 7.38-7.46 (m, 4H), 7.91 (bs, 1H), 8.24 (s, 1H), 8.36 (d, 1H), 11.53 (bs, 1H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ec07e19c10e749fc953ae8c504c8e7ad
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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