HCID 16192989, compound → HCID 67010692, compound

HRID 1630169Notes

Reaction equation

HRID 1630169 reaction equation
Cl.[CH3:2][C:3]([N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)([CH3:7])[C:4]([OH:6])=O.[NH2:13][C@@H:14]([CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)=[O:16]>>[CH2:34]([O:33][CH2:32][C@H:14]([NH:13][C:4](=[O:6])[C:3]([CH3:2])([N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)[CH3:7])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)=[O:16])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 16192989HCID 16192989, compoundHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67010692HCID 67010692, compoundYield 36%

Procedure

Proceeding as in Example 1, but substituting 2-methyl-2-(1H-1,2,4-triazol-1-yl)propanoic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 255, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-methyl-2-(1H-1,2,4-triazol-1-yl)propanamido)propanamide (93.3 mg, 36%). 1H-NMR (400 MHz, CDCl3): δ 8.45 (s, 1H), 8.30 (s, 1H), 8.07 (s, 1H), 7.42 (d, 2H), 7.39-7.24 (m, 7H), 7.11 (d, 1H), 7.05-6.91 (m, 5H), 4.65-4.59 (m, 2H), 4.50 (d, 1H), 4.00 (dd, 1H), 3.58-3.52 (m, 1H), 1.92 (s, 3H), 1.90 (s, 3H). MS (EI) for C28H28FN5O4 found 518 (MH+).

Sources & evidence

ORD record
ord-51f8f460c5524122a415ad8bd3b79488
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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