(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67010672, compound

HRID 1630144Notes

Reaction equation

HRID 1630144 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([OH:15])=O)[CH2:8][CH2:7]1.[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:13](=[O:15])[CH2:12][N:9]1[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][O:3][CH3:2])[CH2:11][CH2:10]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 67009820HCID 67009820, compound

Product 1

HCID 67010672HCID 67010672, compoundYield 41.6%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(2-methoxyethyl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 241, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-(2-methoxyethyl)piperazin-1-yl)acetamido)propanamide (18.8 mg, 41.6%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.93 (d, 1H), 7.59 (d, 2H), 7.30 (m, 5H), 7.21 (t, 2H), 7.03-6.97 (m, 4H), 4.68 (m, 1H), 4.52 (s, 2H), 3.77 (m, 1H), 3.70 (m, 1H), 3.41 (t, 4H), 3.22 (s, 3H), 2.96 (s, 2H), 2.44 (t, 8H). MS (EI) for C31H37FN4O5. found 565.7 (MH+).

Sources & evidence

ORD record
ord-f879846552c0468a8f47a71db4d2cf36
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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