2-Amino-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide → 5-(3-Ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-(2-hydroxy-1-hydroxymethyl-1-methyl-ethylsulfamoyl)-4-methyl-thiazol-2-yl]-amide

HRID 900935Notes

Reaction equation

HRID 900935 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:17]3[N:24]=[CH:25][C:26]([C:27](O)=[O:28])=[C:16]3[N:15]=2)[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH3:2].[OH:30][CH2:31][C:32]([NH:36][S:37]([C:40]1[S:44][C:43]([NH2:45])=[N:42][C:41]=1[CH3:46])(=[O:39])=[O:38])([CH2:34][OH:35])[CH3:33]>>[OH:35][CH2:34][C:32]([NH:36][S:37]([C:40]1[S:44][C:43]([NH:45][C:27]([C:26]2[CH:25]=[N:24][N:17]3[C:18]([C:20]([F:23])([F:21])[F:22])=[CH:19][C:14]([C:6]4[CH:7]=[CH:8][C:9]([C:10]([F:11])([F:12])[F:13])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=4)=[N:15][C:16]=23)=[O:28])=[N:42][C:41]=1[CH3:46])(=[O:39])=[O:38])([CH2:31][OH:30])[CH3:33]

Participants

3

Reactant 2

HCID 866071012-Amino-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amideHCID 866071135-(3-Ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 119964035-(3-Ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-(2-hydroxy-1-hydroxymethyl-1-methyl-ethylsulfamoyl)-4-methyl-thiazol-2-yl]-amide

Procedure

The title compound was prepared from 5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.10) and 2-amino-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (example B.9) according to general procedure II. Light yellow solid. MS (ISP) 681.2 [(M−H)−]; mp 220° C.

Sources & evidence

ORD record
ord-9e7d7e507f344e1ea3e4ad688ae2e650
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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