53958-93-3 → HCID 67009865, compound

HRID 1630100Notes

Reaction equation

HRID 1630100 reaction equation
Cl.[NH:2]1[C:6]([CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:5][N:4]=[CH:3]1.[NH2:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15]>>[NH:2]1[C:6]([CH2:7][CH2:8][C:9]([NH:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)=[O:15])=[O:11])=[CH:5][N:4]=[CH:3]1

Participants

3

Reactant 2

HCID 5736800153958-93-3HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67009865HCID 67009865, compoundYield 5%

Procedure

Proceeding as in Example 1, but substituting 3-(1H-imidazol-5-yl)propanoic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 207, (S)-2-(3-(1H-imidazol-5-yl)propanamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (18.4 mg, 5%). 1H-NMR (400 MHz, DMSO-D6): σ 10.19 (s, 1H), 8.29 (d, 1H), 7.60 (d, 2H), 7.46 (s, 1H), 7.29-7.16 (m, 6H), 7.01-6.94 (m, 4H), 6.73 (s, 1H), 4.70-4.64 (m, 1H), 4.50 (s, 2H), 2.73-2.67 (m, 2H), 2.48-2.43 (m, 4H). MS (EI) for C28H27FN4O4. found 503.2 (MH+).

Sources & evidence

ORD record
ord-0a84175bfa074fa6a5a49cf75d0d2d07
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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