2H-Thiopyran-4-carboxylic acid, 4-aminotetrahydro-, methyl ester, 1,1-dioxide → HCID 67272137, compound

HRID 1409534Notes

Reaction equation

HRID 1409534 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])=[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[CH:10]=[N:9][C:8]=12)(O)=[O:2].[NH2:28][C:29]1([C:37]([O:39][CH3:40])=[O:38])[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[CH2:31][CH2:30]1>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:7]3[N:6]=[CH:5][C:4]([C:1](=[O:2])[NH:28][C:29]4([C:37]([O:39][CH3:40])=[O:38])[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[CH2:31][CH2:30]4)=[C:8]3[N:9]=[CH:10][C:11]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[C:14]([F:20])[CH:15]=1

Participants

3

Reactant 2

HCID 615632892H-Thiopyran-4-carboxylic acid, 4-aminotetrahydro-, methyl ester, 1,1-dioxideHCID 67273104HCID 67273104, compound

Product 1

HCID 67272137HCID 67272137, compoundYield 79%

Procedure

The compound obtained in Reference Example A11 (3-carboxy-7-(4-chloro-2-fluorophenyl)-6-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine; 39 mg) and methyl 4-amino-1,1-dioxotetrahydrothiopyran-4-carboxylate (20 mg) were treated in the same manner as described in Example A1 to give 7-(4-chloro-2-fluorophenyl)-6-(2-chlorophenyl)-3-[N-(4-methoxycarbonyl-1,1-dioxotetrahydrothiopyran-4-yl)-carbamoyl]pyrazolo[1,5-a]pyrimidine (45 mg, yield: 79%) as a pale yellow powder.

Workup

  1. additionwere treated in the same manner

Sources & evidence

ORD record
ord-5c6d9e87ecb945848f3aadd53543ed48
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Reaction notes

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