(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009806, compound

HRID 1630146Notes

Reaction equation

HRID 1630146 reaction equation
Cl.[Cl:2][C:3]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([OH:15])=O)[CH2:8][CH2:7]1.[NH2:21][C@@H:22]([CH2:40][O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:28][CH:27]=1)=[O:24]>>[CH2:42]([O:41][CH2:40][C@H:22]([NH:21][C:13](=[O:15])[CH2:12][N:9]1[CH2:8][CH2:7][N:6]([CH2:5][C:4]2[C:16]([F:20])=[CH:17][CH:18]=[CH:19][C:3]=2[Cl:2])[CH2:11][CH2:10]1)[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:28][CH:27]=1)=[O:24])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 670102141222197-49-0

Product 1

HCID 67009806HCID 67009806, compoundYield 40.1%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(2-chloro-6-fluorobenzyl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 239, (S)-3-(benzyloxy)-2-(2-(4-(2-chloro-6-fluorobenzyl)piperazin-1-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (20.8 mg, 40.1%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.93 (d, 1H), 7.60 (d, 2H), 7.37 (m, 2H), 7.29 (m, 5H), 7.21 (t, 3H), 7.04-6.98 (m, 4H), 4.68 (m, 1H), 4.51 (s, 2H), 3.77 (m, 1H), 3.70 (m, 1H), 3.60 (s, 2H), 2.96 (m, 2H), 2.51 (m, 8H). MS (EI) for C35H35ClF2N4O4. found 650.1 (MH+).

Sources & evidence

ORD record
ord-bdfd9a18154a40d38ef98eb47bdbd92f
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…