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

HRID 908617Notes

Reaction equation

HRID 908617 reaction equation
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:32]=[CH:31][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][NH:16][CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][CH:5]=1.Cl[C:36]1[S:37][C:38]2[C:43]([Cl:44])=[N:42][C:41]([CH:45]3[CH2:47][CH2:46]3)=[N:40][C:39]=2[N:48]=1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:34][C:2]([F:1])([F:33])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:36]3[S:37][C:38]4[C:43]([Cl:44])=[N:42][C:41]([CH:45]5[CH2:46][CH2:47]5)=[N:40][C:39]=4[N:48]=3)[CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 597037622,7-Dichloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidineHCID 59703788(R)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

Product 1

HCID 59703811(R)-4-(7-chloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideYield 93.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixed solution of the compound (0.75 g) obtained in Step 2 and 2,7-dichloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidine (0.36 g) in chloroform (7.5 ml) was added at room temperature N,N-diisopropylethylamine (0.31 ml). After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:3-3:2) to give the title compound (0.99 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:3-3:2)

Sources & evidence

ORD record
ord-1e57917d54f04408bc4c239f96a60249
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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