(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 45376626, compound

HRID 1630170Notes

Reaction equation

HRID 1630170 reaction equation
Cl.[CH3:2][C:3]1[N:7]=[C:6]([CH3:8])[N:5]([CH2:9][C:10]([OH:12])=O)[N:4]=1.[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:10](=[O:12])[CH2:9][N:5]1[C:6]([CH3:8])=[N:7][C:3]([CH3:2])=[N:4]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])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 670101702-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)acetic acid hydrochloride

Product 1

HCID 45376626HCID 45376626, compoundYield 27%

Procedure

Proceeding as in Example 1, but substituting 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 256, (S)-3-(benzyloxy)-2-(2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (219 mg, 27%). 1H-NMR (400 MHz, CDCl3): σ 8.38 (s, 1H), 7.40-7.16 (m, 7H), 7.05-6.92 (m, 5H), 4.74 (s, 2H), 4.70-4.64 (m, 3H), 4.55 (d, 1H), 4.02-3.97 (m, 1H), 3.62-3.56 (m, 1H), 2.44 (s, 3H), 2.33 (s, 3H). MS (EI) for C28H28FN5O4. found 518.0 (MH+).

Sources & evidence

ORD record
ord-85e00ed88bbe4c65a7a89ead3b615895
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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