Piperazin-4-ylacetophenone → 1-(4-{4-[(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidine-2-carbonyl]-piperazin-1-yl}-phenyl)-ethanone

HRID 490599Notes

Reaction equation

HRID 490599 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.[N:33]1([C:39]2[CH:44]=[CH:43][C:42]([C:45](=[O:47])[CH3:46])=[CH:41][CH:40]=2)[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]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:36]1[CH2:37][CH2:38][N:33]([C:39]2[CH:40]=[CH:41][C:42]([C:45](=[O:47])[CH3:46])=[CH:43][CH:44]=2)[CH2:34][CH2:35]1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 97269Piperazin-4-ylacetophenoneHCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

Product 1

HCID 688611511-(4-{4-[(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidine-2-carbonyl]-piperazin-1-yl}-phenyl)-ethanoneYield 8.1%

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-(4-piperazine-1-yl-phenyl)-ethanone instead of 2-piperazin-1-yl-benzonitrile, to the title compound (5.8 mg, 8.1%) as light yellow oil. MS m/e=559.4 [M+H]+.

Sources & evidence

ORD record
ord-402236c1234845948d9fa091f3263b77
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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