(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67010681, compound

HRID 1630150Notes

Reaction equation

HRID 1630150 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[NH2:18][C@@H:19]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)=[O:21]>>[CH2:39]([O:38][CH2:37][C@H:19]([NH:18][C:15](=[O:17])[CH2:14][N:11]1[CH2:10][CH2:9][CH:8]([N:5]2[CH2:4][CH2:3][O:2][CH2:7][CH2:6]2)[CH2:13][CH2:12]1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)=[O:21])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67009176HCID 67009176, compound

Product 1

HCID 67010681HCID 67010681, compoundYield 47.4%

Procedure

Proceeding as in Example 1, but substituting 2-(4-morpholinopiperidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 105, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-morpholinopiperidin-1-yl)acetamido)propanamide (22.4 mg, 47.4%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.94 (d, 1H), 7.60 (d, 2H), 7.30 (m, 5H), 7.22 (t, 2H), 7.03-6.98 (m, 4H), 4.69 (m, 1H), 4.52 (s, 2H), 3.78 (m, 1H), 3.70 (m, 1H), 3.56 (t, 4H), 2.96-2.83 (m, 4H), 2.41 (m, 4H), 2.05 (m, 3H), 1.73 (m, 2H), 1.39 (m, 2H). MS (EI) for C33H39FN4O5. found 591.7 (MH+).

Sources & evidence

ORD record
ord-0818a33101cb4b7595199b4b1e439125
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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