(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67010444, compound

HRID 1630132Notes

Reaction equation

HRID 1630132 reaction equation
Cl.[N:2]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([OH:16])=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[NH2:17][C@@H:18]([CH2:36][O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)=[O:20]>>[CH2:38]([O:37][CH2:36][C@H:18]([NH:17][C:14](=[O:16])[CH2:13][N:10]1[CH2:9][CH2:8][CH:7]([N:2]2[CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:12][CH2:11]1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)=[O:20])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67010089HCID 67010089, compound

Product 1

HCID 67010444HCID 67010444, compoundYield 48.1%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(pyrrolidin-1-yl)piperidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 43, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-(pyrrolidin-1-yl)piperidin-1-yl)acetamido)propanamide (22.1 mg, 48.1%). 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 7.96 (d, 1H), 7.59 (d, 2H), 7.30 (m, 5H), 7.21 (m, 2H), 7.01 (m, 4H), 4.68 (m, 1H), 4.52 (s, 2H), 3.75 (m, 2H), 3.25 (m, 2H), 2.95 (s, 2H), 2.83 (m, 2H), 2.09 (t, 2H), 2.00 (m, 1H), 1.79 (m, 2H), 1.68 (m, 5H), 1.44 (m, 2H). MS (EI) for C33H39FN4O4: 575.8 (MH+).

Sources & evidence

ORD record
ord-54a626dcb73d4d68bb91e02cded54dd2
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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