(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009279, compound

HRID 1630133Notes

Reaction equation

HRID 1630133 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]([OH:19])=O)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[NH2:20][C@@H:21]([CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)=[O:23]>>[CH2:41]([O:40][CH2:39][C@H:21]([NH:20][C:17](=[O:19])[CH2:16][N:13]1[CH2:12][CH2:11][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=2)[CH2:15][CH2:14]1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)=[O:23])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67010063HCID 67010063, compound

Product 1

HCID 67009279HCID 67009279, compoundYield 32%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(3-methoxyphenyl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 42, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-(3-methoxyphenyl)piperazin-1-yl)acetamido)propanamide (15.7 mg, 32%). 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 8.01 (d, 1H), 7.60 (d, 2H), 7.26 (m, 7H), 7.11 (t, 1H), 7.01 (m, 4H), 6.50 (d, 1H), 6.43 (s, 1H), 6.37 (d, 1H), 4.70 (m, 1H), 4.52 (s, 2H), 3.77 (m, 1H), 3.73 (m, 4H), 3.13 (m, 4H), 3.06 (s, 2H), 2.61 (m, 4H). MS (EI) for C35H37FN4O5: 613.7 (MH+).

Sources & evidence

ORD record
ord-2586f780c760415b990da3678bcfb66e
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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