Diisopropylethylamine → (R)-4-(7-chloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

HRID 908646Notes

Reaction equation

HRID 908646 reaction equation
Cl[C:2]1[S:3][C:4]2[C:9]([Cl:10])=[N:8][C:7]([C:11]([F:14])([F:13])[F:12])=[N:6][C:5]=2[N:15]=1.[F:16][C:17]([F:48])([F:47])[O:18][C:19]1[CH:46]=[CH:45][C:22]([CH2:23][NH:24][C:25]([C@H:27]2[CH2:32][NH:31][CH2:30][CH2:29][N:28]2[S:33]([C:36]2[CH:41]=[CH:40][C:39]([CH:42]3[CH2:44][CH2:43]3)=[CH:38][CH:37]=2)(=[O:35])=[O:34])=[O:26])=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:48][C:17]([F:16])([F:47])[O:18][C:19]1[CH:46]=[CH:45][C:22]([CH2:23][NH:24][C:25]([C@H:27]2[CH2:32][N:31]([C:2]3[S:3][C:4]4[C:9]([Cl:10])=[N:8][C:7]([C:11]([F:14])([F:13])[F:12])=[N:6][C:5]=4[N:15]=3)[CH2:30][CH2:29][N:28]2[S:33]([C:36]2[CH:41]=[CH:40][C:39]([CH:42]3[CH2:43][CH2:44]3)=[CH:38][CH:37]=2)(=[O:34])=[O:35])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59703776(R)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideHCID 597038262,7-Dichloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidine

Product 1

HCID 59703751(R)-4-(7-chloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideYield 102.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixed solution of the compound (27 mg) obtained in Example 1001, Step 8, the compound (43 mg) obtained in Step 4 and chloroform (0.50 ml) was added N,N-diisopropylethylamine (19 μl) under ice-cooling. After stirring overnight at room temperature, the reaction mixture was purified by silica gel column chromatography (chloroform:methanol=20:1) to give the title compound (66 mg).

Workup

  1. temperaturecooling
  2. customthe reaction mixture was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-cac53cd31eef4af38e6687a0f06992ca
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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