(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 45376498, compound
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
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 230, (S)-2-(2-(4-acetylpiperazin-1-yl)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (13.4 mg, 31.3%). 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 8.03 (d, 1H), 7.99 (s, 1H), 7.61 (d, 2H), 7.30 (m, 5H), 7.21 (t, 2H), 7.00 (m, 4H), 4.70 (m, 1H), 4.52 (s, 2H), 3.73 (m, 2H), 3.34 (m, 4H), 3.06 (s, 2H), 2.41 (m, 4H). MS (EI) for C29H31FN4O5: 535.4 (MH+).
Sources & evidence
- ORD record
- ord-cd14209de6a0455ca80535a320a41d95
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791102B2
Reaction notes
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