1,1-dimethylethyl (2S)-4-{[5'-(aminomethyl)-2'-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylate → N-[(6-fluoro-3'-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-3-(4-piperidinyl)benzamide

HRID 2080331Notes

Reaction equation

HRID 2080331 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:30])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[C@@H:18]([CH3:29])[CH2:17]3)[CH:10]=2)[CH:8]=1.CC(OC([N:38]1[CH2:43][CH2:42][CH:41]([C:44]2[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=2)[C:47]([OH:49])=O)[CH2:40][CH2:39]1)=O)(C)C>>[F:30][C:6]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:21][CH2:20][NH:19][C@@H:18]([CH3:29])[CH2:17]3)[CH:10]=2)=[CH:8][C:3]([CH2:2][NH:1][C:47](=[O:49])[C:46]2[CH:50]=[CH:51][CH:52]=[C:44]([CH:41]3[CH2:40][CH2:39][NH:38][CH2:43][CH2:42]3)[CH:45]=2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 251325161,1-dimethylethyl (2S)-4-{[5'-(aminomethyl)-2'-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylateHCID 450737913-(1-(tert-Butoxycarbonyl)piperidin-4-yl)benzoic acid

Product 1

HCID 11706021N-[(6-fluoro-3'-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-3-(4-piperidinyl)benzamideYield 18%

Procedure

Following the standard procedure outlined in Example 57, 1,1-dimethylethyl (2S)-4-{[5′-(aminomethyl)-2′-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylate, 50 mg, 0.121 mmol) was reacted with the commercially available 3-(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinyl)benzoic acid (37 mg, 0.121 mmol) to give the title compound (11 mg, 18%). LC/MS: m/z, 501 (M+H), 1.27 min.

Sources & evidence

ORD record
ord-569109b5d30d485d9dbfb859e3d7db9e
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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