HCID 46735976, compound → HCID 67009158, compound

HRID 1630129Notes

Reaction equation

HRID 1630129 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]([OH:12])=O)[CH2:4]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[CH2:6][CH2:7][CH2:8][CH:3]([CH3:2])[CH2:4]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 46735976HCID 46735976, compoundHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67009158HCID 67009158, compoundYield 42.8%

Procedure

Proceeding as in Example 1, but substituting 2-(3-methylpiperidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 46, (2S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(3-methylpiperidin-1-yl)acetamido)propanamide (17.8 mg, 42.8%). 1H-NMR (400 MHz, DMSO-D6): σ 10.20 (s, 1H), 7.94 (d, 1H), 7.56 (d, 2H), 7.29 (m, 5H), 7.21 (m, 2H), 7.01 (m, 4H), 4.69 (m, 1H), 4.52 (s, 2H), 3.73 (m, 2H), 2.93 (m, 2H), 2.73 (m, 2H), 1.98 (s, 1H), 1.58 (m 5H), 0.81 (m, 4H). MS (EI) for C30H34FN3O4: 520.7 (MH+).

Sources & evidence

ORD record
ord-273ebcbf8bf349f1a6677f1662665084
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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