(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 45376498, compound

HRID 1630135Notes

Reaction equation

HRID 1630135 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]1)(=[O:4])[CH3:3].[NH2:15][C@@H:16]([CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[O:18]>>[C:2]([N:5]1[CH2:6][CH2:7][N:8]([CH2:11][C:12]([NH:15][C@@H:16]([CH2:34][O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:24][CH:25]=2)=[O:18])=[O:14])[CH2:9][CH2:10]1)(=[O:4])[CH3:3]

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67010654HCID 67010654, compound

Product 1

HCID 45376498HCID 45376498, compoundYield 32.8%

Procedure

Proceeding as in Example 1, but substituting 2-(4-acetylpiperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 236, (S)-2-(2-(4-acetylpiperazin-1-yl)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (14.4 mg, 32.8%). 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 8.01 (d, 1H), 7.60 (d, 2H), 7.30 (s, 5H), 7.20 (t, 2H), 7.02 (m, 4H), 4.70 (m, 1H), 4.52 (s, 2H), 3.74 (m, 2H), 3.41 (m, 5H), 3.03 (s, 2H), 2.40 (m, 3H), 1.98 (s, 3H). MS (EI) for C30H33FN4O5: 549.7 (MH+).

Sources & evidence

ORD record
ord-26f3747c197c43cfbaaa8d1239206082
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…