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

HRID 908610Notes

Reaction equation

HRID 908610 reaction equation
[F:1][C:2]([F:35])([F:34])[O:3][C:4]1[CH:33]=[CH:32][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]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][CH:5]=1.Cl[C:37]1[S:38][C:39]2[C:44]([Cl:45])=[N:43][C:42]([CH:46]3[CH2:48][CH2:47]3)=[N:41][C:40]=2[N:49]=1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:35][C:2]([F:1])([F:34])[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:37]3[S:38][C:39]4[C:44]([Cl:45])=[N:43][C:42]([CH:46]5[CH2:47][CH2:48]5)=[N:41][C:40]=4[N:49]=3)[CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=2)(=[O:19])=[O:20])=[O:11])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 597037622,7-Dichloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidineHCID 59703800(R)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

Product 1

HCID 59703729(R)-4-(7-chloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixed solution of the compound (0.94 g) obtained in Example 783, the compound (0.48 g) obtained in Step 5 and chloroform (2.8 ml) was added N,N-diisopropylethylamine (0.30 ml) at room temperature. The mixture was stirred at room temperature for 30 min, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:chloroform=1:2) to give the title compound (1.3 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate:chloroform=1:2)

Sources & evidence

ORD record
ord-15b5161cf4d14561a24999de1f89efca
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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