Azepan-1-ylacetic acid hydrochloride → HCID 45377860, compound

HRID 1630120Notes

Reaction equation

HRID 1630120 reaction equation
Cl.[N:2]1([CH2:9][C:10]([OH:12])=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]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]>>[N:2]1([CH2:9][C:10]([NH:13][C@@H:14]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[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:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 43810773Azepan-1-ylacetic acid hydrochlorideHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 45377860HCID 45377860, compoundYield 52.2%

Procedure

Proceeding as in Example 1, but substituting 2-(azepan-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 128, (S)-2-(2-(azepan-1-yl)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (21.7 mg, 52.2%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): 10.22 (s, 1H), 7.99 (d, 1H), 7.60 (d, 2H), 7.27-7.33 (m, 5H), 7.19-7.23 (m, 2H), 6.99-7.04 (m, 4H), 4.70 (m, 1H), 4.52 (s, 2H), 3.67-3.79 (m, 2H), 3.10 (m, 2H), 2.51-2.63 (m, 4H), 1.55-1.60 (m, 8 h). MS (EI) for C30H34FN3O4. found 520.6 (MH+).

Sources & evidence

ORD record
ord-2e4676ab93d84912a048b19cea36ddaf
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…