(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 45377856, compound

HRID 1630140Notes

Reaction equation

HRID 1630140 reaction equation
Cl.[F:2][C:3]([F:21])([F:20])[C:4]1[C:5]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]([OH:19])=O)[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1.[NH2:22][C@@H:23]([CH2:41][O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[CH:29][CH:28]=1)=[O:25]>>[CH2:43]([O:42][CH2:41][C@H:23]([NH:22][C:17](=[O:19])[CH2:16][N:13]1[CH2:12][CH2:11][N:10]([C:5]2[C:4]([C:3]([F:2])([F:21])[F:20])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:15][CH2:14]1)[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[CH:29][CH:28]=1)=[O:25])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67010700HCID 67010700, compound

Product 1

HCID 45377856HCID 45377856, compoundYield 32.4%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 112, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)acetamido)propanamide (16.9 mg, 32.4%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.23 (s, 1H), 8.54 (d, 1H), 8.06 (t, 2H), 7.61 (d, 2H), 7.30 (m, 4H), 7.27-7.19 (m, 4H), 7.04-6.98 (m, 4H), 4.72 (m, 1H), 4.53 (s, 2H), 3.76 (m, 2H), 3.20 (t, 4H), 3.08 (s, 2H), 2.63 (m, 4H). MS (EI) for C34H33F4N5O4. found 652.6 (MH+).

Sources & evidence

ORD record
ord-4e3afd88893641a08bd4055d1a0963d3
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…