(S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 178454578, compound

HRID 1630104Notes

Reaction equation

HRID 1630104 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=O)[N:4]=[CH:3]1.[NH2:13][C@@H:14]([CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[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]>>[NH:2]1[CH:6]=[C:5]([C:7]([CH3:12])([CH3:11])[C:8]([NH:13][C@@H:14]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:22][CH:23]=2)=[O:16])=[O:10])[N:4]=[CH:3]1

Participants

3

Reactant 2

HCID 67009398(S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 178454672HCID 178454672, compound

Product 1

HCID 178454578HCID 178454578, compoundYield 60%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-imidazol-4-yl)-2-methylpropanoic acid hydrochloride and (S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 161, (S)-2-(2-(1H-imidazol-4-yl)-2-methylpropanamido)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (92.2 mg, 60%). 1H-NMR (400 MHz, CDCl3): δ 9.31 (s, 1H), 8.32 (br s, 1H), 7.49-7.45 (m, 3H), 7.38 (d, 1H), 7.22-7.18 (m, 2H), 7.02-6.88 (m, 7H), 6.83 (s, 1H), 4.72-4.68 (m, 1H), 4.51 (d, 1H), 4.44 (d, 1H), 4.04 (dd, 1H), 3.63 (dd, 1H), 1.56 (s, 3H), 1.55 (s, 3H). MS (EI) for C29H29F2N4O4 found 535 (MH+).

Sources & evidence

ORD record
ord-d8a5b501caf94ef1b2d0b63acacb08b5
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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