(4-Methylpiperidin-1-yl)acetic acid hydrochloride → HCID 67009213, compound

HRID 1630116Notes

Reaction equation

HRID 1630116 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]([OH:12])=O)[CH2:5][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:6]1[CH2:5][CH2:4][CH:3]([CH3:2])[CH2:8][CH2:7]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 17389852(4-Methylpiperidin-1-yl)acetic acid hydrochlorideHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67009213HCID 67009213, compoundYield 46.2%

Procedure

Proceeding as in Example 1, but substituting 2-(4-methylpiperidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 130, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-methylpiperidin-1-yl)acetamido)propanamide (19.2 mg, 46.2%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.94 (d, 1H), 7.60 (d, 2H), 7.29-7.33 (m, 5H), 7.19-7.27 (m, 2H), 6.98-7.04 (m, 4H), 4.67-4.71 (m, 1H), 4.52 (s, 2H), 3.68-0.80 (m, 2H), 2.94 (d, 2H), 2.77-2.90 (m, 2H), 2.00-2.06 (m, 2H), 1.54-1.60 (m, 2H), 1.30-1.33 (m, 1H), 1.13-1.19 (m, 2H), 0.89 (d, 3H). MS (EI) for C30H34FN3O4. found 520.6 (MH+).

Sources & evidence

ORD record
ord-101fc3576de64f9fa5a0e485eb900131
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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