4-Methoxycinnamic Acid → N-[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-3-(4-methoxy-phenyl)-N-(4-pentyl-benzyl)-acrylamide

HRID 563136Notes

Reaction equation

HRID 563136 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:36])[C@@H:15]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:27][CH:26]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37][O:38][C:39]1[CH:49]=[CH:48][C:42](/[CH:43]=[CH:44]/[C:45](O)=[O:46])=[CH:41][CH:40]=1>>[CH2:16]([C@H:15]([N:23]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:29][CH:30]=1)[C:45](=[O:46])[CH:44]=[CH:43][C:42]1[CH:48]=[CH:49][C:39]([O:38][CH3:37])=[CH:40][CH:41]=1)[C:14]([N:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1)=[O:36])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 6994144-Methoxycinnamic AcidHCID 598082551-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-one

Product 1

HCID 67005100N-[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-3-(4-methoxy-phenyl)-N-(4-pentyl-benzyl)-acrylamideYield 48%

Procedure

Acylation of 1-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-one (43.5 mg, 0.09 mmol) according to the procedure described for the preparation of Example 1 with trans-4-methoxy-cinnamic acid (17.6 mg, 0.099 mmol) gave 27.7 mg (48%) of N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-3-(4-methoxy-phenyl)-N-(4-pentyl-benzyl)-acrylamide. LC-MS: tR=1.00 min; [M+H]+=644.50.

Sources & evidence

ORD record
ord-a194a232167a4b0aaf26e0b9e7983ee0
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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