(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67010422, compound

HRID 1630149Notes

Reaction equation

HRID 1630149 reaction equation
Cl.[CH2:2]([N:4]([CH2:14][CH3:15])[CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([OH:13])=O)[CH2:6]1)[CH3:3].[NH2:16][C@@H:17]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19]>>[CH2:37]([O:36][CH2:35][C@H:17]([NH:16][C:11](=[O:13])[CH2:10][N:7]1[CH2:8][CH2:9][CH:5]([N:4]([CH2:2][CH3:3])[CH2:14][CH3:15])[CH2:6]1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67009777HCID 67009777, compound

Product 1

HCID 67010422HCID 67010422, compoundYield 48.2%

Procedure

Proceeding as in Example 1, but substituting 2-(3-(diethylamino)pyrrolidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 109, (2S)-3-(benzyloxy)-2-(2-(3-(diethylamino)pyrrolidin-1-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (21.7 mg, 48.2%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 7.87 (d, 1H), 7.61 (d, 2H), 7.29 (m, 5H), 7.21 (t, 2H), 7.03-6.98 (m, 4H), 4.71 (m, 1H), 4.52 (s, 2H), 3.76-3.67 (m, 2H), 3.31 (m, 1H), 3.15 (m, 1H), 3.03 (m, 1H), 2.69-2.58 (m, 3H), 2.48 (m, 5H), 1.88 (m, 1H), 1.55 (m, 1H), 0.92 (t, 6H). MS (EI) for C32H39FN4O4. found 563.7 (MH+).

Sources & evidence

ORD record
ord-ee5386c5e87644ab96843e478a5ba3f9
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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