(4-Phenylpiperazin-1-yl)acetic acid--hydrogen chloride (1/1) → HCID 67009523, compound

HRID 1630110Notes

Reaction equation

HRID 1630110 reaction equation
Cl.[C:2]1([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH: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][N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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 17221240(4-Phenylpiperazin-1-yl)acetic acid--hydrogen chloride (1/1)HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67009523HCID 67009523, compoundYield 28.7%

Procedure

Proceeding as in Example 1, but substituting 2-(4-phenylpiperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 225, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-phenylpiperazin-1-yl)acetamido)propanamide (13.4 mg, 28.7%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.23 (s, 1H), 8.02 (s, 1H), 7.60 (d, 2H), 7.28-7.29 (m, 4H), 7.19-7.26 (m, 5H), 6.99-7.04 (m, 4H), 6.92 (d, 2H), 6.78 (t, 1H), 4.71 (m, 1H), 4.52 (s, 2H), 3.76 (m, 2H), 3.13 (m, 4H), 3.07 (s, 2H), 2.63 (m, 4H). MS (EI) for C34H35FN4O4. found 583.6 (MH+).

Sources & evidence

ORD record
ord-0934bac5a6bb481fab5d9a7534a5bd98
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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