2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid → 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [1-(1,1-dimethyl-2-Pyrrolidin-1-yl-ethyl)-1H-imidazol-4-yl]-amide

HRID 553186Notes

Reaction equation

HRID 553186 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[CH2:8][CH:7]([NH:13][CH:14]([CH2:18][CH2:19][CH3:20])[C:15]([OH:17])=O)[CH2:6][CH2:5]2.[CH3:21][C:22]([N:30]1[CH:34]=[C:33]([N+:35]([O-])=O)[N:32]=[CH:31]1)([CH3:29])[CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH3:29][C:22]([N:30]1[CH:34]=[C:33]([NH:35][C:15](=[O:17])[CH:14]([NH:13][CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[C:10]([F:12])[CH:11]=[C:2]([F:1])[CH:3]=3)[CH2:8]2)[CH2:18][CH2:19][CH3:20])[N:32]=[CH:31]1)([CH3:21])[CH2:23][N:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 211128022-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acidHCID 671651351-(1,1-Dimethyl-2-pyrrolidin-1-yl-ethyl)4-nitro-1H-imidazole

Product 1

HCID 115473862-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [1-(1,1-dimethyl-2-Pyrrolidin-1-yl-ethyl)-1H-imidazol-4-yl]-amide

Procedure

Following the procedure for Example 86, 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid (diastereomer 1) was reacted with 1-(1,1-Dimethyl-2-pyrrolidin-1-yl-ethyl)-4-nitro-1H-imidazole to afford the title compound: C13 NMR (100 MHz, CDCl3) 14.2, 19.6, 24.3, 26.6, 28.2, 28.6, 29.6, 36.6, 51.9, 56.0, 59.3, 60.3, 67.2, 100.8, 101.0, 101.3, 104.9, 110.7, 112.5, 130.8, 172.6; MS m/z 474.3 (M+1).

Sources & evidence

ORD record
ord-6870ea8795394b5386be6a6f5b73f7fb
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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