(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67010217, compound

HRID 1630137Notes

Reaction equation

HRID 1630137 reaction equation
Cl.[CH2:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([OH:13])=O)[CH2:6][CH2:5]1)[CH3:3].[NH2:14][C@@H:15]([CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17]>>[CH2:35]([O:34][CH2:33][C@H:15]([NH:14][C:11](=[O:13])[CH2:10][N:7]1[CH2:6][CH2:5][N:4]([CH2:2][CH3:3])[CH2:9][CH2:8]1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 670106301216609-00-5

Product 1

HCID 67010217HCID 67010217, compoundYield 48.2%

Procedure

Proceeding as in Example 1, but substituting 2-(4-ethylpiperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 114, (S)-3-(benzyloxy)-2-(2-(4-ethylpiperazin-1-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (20.6 mg, 48.2%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.93 (d, 1H), 7.60 (d, 2H), 7.31-7.25 (m, 5H), 7.21 (t, 2H), 7.04-6.99 (m, 4H), 4.69 (m, 1H), 4.51 (s, 2H), 3.76 (m, 1H), 3.71 (m, 1H), 2.97 (s, 2H), 2.46 (m, 3H), 2.38 (m, 3H), 2.33-2.28 (m, 4H), 0.98 (t, 3H). MS (EI) for C30H35FN4O4. found 535.6 (MH+).

Sources & evidence

ORD record
ord-609e99fa29e94343bfbb5dd446384f28
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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