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-[2-(2,6-dimethyl-morpholin-4-yl)-1,1-dimethyl-ethyl]-1H-imidazol-4-yl}-amide

HRID 1392542Notes

Reaction equation

HRID 1392542 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][CH:22]1[O:27][CH:26]([CH3:28])[CH2:25][N:24]([CH2:29][C:30]([N:33]2[CH:37]=[C:36]([NH2:38])[N:35]=[CH:34]2)([CH3:32])[CH3:31])[CH2:23]1>>[CH3:28][CH:26]1[O:27][CH:22]([CH3:21])[CH2:23][N:24]([CH2:29][C:30]([N:33]2[CH:37]=[C:36]([NH:38][C:15](=[O:17])[CH:14]([NH:13][CH:7]3[CH2:6][CH2:5][C:4]4[C:9](=[C:10]([F:12])[CH:11]=[C:2]([F:1])[CH:3]=4)[CH2:8]3)[CH2:18][CH2:19][CH3:20])[N:35]=[CH:34]2)([CH3:32])[CH3:31])[CH2:25]1

Participants

3

Reactant 2

HCID 211128022-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acidHCID 67164004HCID 67164004, compound

Product 1

HCID 115119092-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid {1-[2-(2,6-dimethyl-morpholin-4-yl)-1,1-dimethyl-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 2) was reacted with 1-[2-(2,6-Dimethyl-morpholin-4-yl)-1,1-dimethyl-ethyl]-1H-imidazol-4-ylamine to afford the title compound: C13 NMR (100 MHz, CDCl3) 14.1, 19.1, 19.5, 25.9, 28.2, 28.9, 29.7, 36.6, 38.8, 53.0, 58.9, 61.0, 61.3, 68.5, 72.1, 74.4, 76.9, 77.3, 77.6, 100.8, 101.1, 101.3, 104.7, 110.7, 110.9, 117.9, 131.2, 137.3, 139.8, 159.8, 162.3, 172.3; MS m/z 518.2 (M+1).

Sources & evidence

ORD record
ord-07da62bd82cd4b399d8f85eebbac3569
Source dataset
uspto-grants-2008_03
Patent number
US07342118B2

Reaction notes

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