1-[3-(Trifluoromethyl)pyridin-2-yl]piperazine → [(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-methanone

HRID 490597Notes

Reaction equation

HRID 490597 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([N:13](C(OC(C)(C)C)=O)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:10][CH:9]1[C:30](O)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:33][C:34]([F:48])([F:47])[C:35]1[C:36]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[N:37][CH:38]=[CH:39][CH:40]=1>>[CH2:1]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:10][C@H:9]1[C:30]([N:44]1[CH2:43][CH2:42][N:41]([C:36]2[C:35]([C:34]([F:33])([F:47])[F:48])=[CH:40][CH:39]=[CH:38][N:37]=2)[CH2:46][CH2:45]1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27777861-[3-(Trifluoromethyl)pyridin-2-yl]piperazineHCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

Product 1

HCID 67546668[(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-methanoneYield 7.5%

Procedure

As described for Example 1f, 1-benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid (60.0 mg, 0.134 mmol) was converted, using 1-(3-trifluoromethyl-pyridin-2-yl)-piperazine instead of 2-piperazin-1-yl-benzonitrile, to the title compound (5.7 mg, 7.5%) as light yellow oil. MS m/e=560.4 [M+H]+.

Sources & evidence

ORD record
ord-20bbcc2cf56d4ca9b6699f77c4a535e8
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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