4-bromo-1H-pyrazolo[4,3-c]pyridin-3-amine → N-(2-{3-[4-(3-amino-1H-pyrazolo[4,3-c]pyrid-4-yl)phenyl]ureido}-4-trifluoromethylphenyl)acetamide

HRID 1677640Notes

Reaction equation

HRID 1677640 reaction equation
Br[C:2]1[C:7]2[C:8]([NH2:11])=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:43])[NH:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:30]=3[NH:39][C:40](=[O:42])[CH3:41])=[CH:22][CH:21]=2)O1>>[NH2:11][C:8]1[C:7]2[C:2]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:43])[NH:28][C:29]4[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:30]=4[NH:39][C:40](=[O:42])[CH3:41])=[CH:22][CH:21]=3)=[N:3][CH:4]=[CH:5][C:6]=2[NH:10][N:9]=1

Participants

3

Reactant 2

HCID 583807624-bromo-1H-pyrazolo[4,3-c]pyridin-3-amineHCID 67329019N-(2-{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureido}-4-trifluoromethylphenyl)acetamide

Product 1

HCID 24897406N-(2-{3-[4-(3-amino-1H-pyrazolo[4,3-c]pyrid-4-yl)phenyl]ureido}-4-trifluoromethylphenyl)acetamide

Procedure

4-Bromo-1H-pyrazolo[4,3-c]pyrid-3-ylamine and N-(2-{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureido}-4-trifluoromethylphenyl)acetamide are coupled by Suzuki reaction according to a protocol similar to that for the preparation of Example 10. A yellow powder of N-(2-{3-[4-(3-amino-1H-pyrazolo[4,3-c]pyrid-4-yl)phenyl]ureido}-4-trifluoromethylphenyl)acetamide is obtained, the characteristics of which are as follows:

Workup

  1. customfor the preparation of Example 10

Sources & evidence

ORD record
ord-d036bc437bc0470698e8a6541a174305
Source dataset
uspto-grants-2011_08
Patent number
US08008322B2

Reaction notes

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