(4-Benzyl-piperazin-1-yl)-acetic acid → HCID 49780166, compound

HRID 929507Notes

Reaction equation

HRID 929507 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1.[CH2:22]([N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36](O)=[O:37])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([N:29]1[CH2:30][CH2:31][N:32]([CH2:35][C:36]([N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=3)=[O:9])[CH2:3][CH2:2]2)=[O:37])[CH2:33][CH2:34]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 1402890(4-Benzyl-piperazin-1-yl)-acetic acidHCID 49780164HCID 49780164, compound

Product 1

HCID 49780166HCID 49780166, compound

Procedure

Intermediate 42 (303 mg, 1 mmol) was reacted with carboxylic acid 46 by Method E. Flash chromatography eluted with 9:1 DCM:MeOH afforded compound 50 (379 mg, 73%) as a white solid: Mp 178-183° C. 1H NMR (500 MHz, DMSO-d6) δ 8.52 (s, 1H), 7.47 (d, J=8.9 Hz, 2H), 7.34-7.26 (m, 4H), 7.26-7.19 (m, 3H), 6.25 (d, J=7.5 Hz, 1H), 4.14 (d, J=13.4 Hz, 1H), 3.95 (d, J=12.5 Hz, 1H), 3.75-3.66 (m, 1H), 3.45 (s, 2H), 3.23 (d, J=13.2 Hz, 1H), 3.12 (t, J=11.9 Hz, 1H), 3.00 (d, J=13.1 Hz, 1H), 2.78 (t, J=11.6 Hz, 1H), 2.47-2.30 (m, 8H), 1.89-1.76 (m, 2H), 1.40-1.31 (m, 1H), 1.23-1.13 (m, 1H). Purity 90%. HRMS calculated for C20H21F3N4O3−H+ 518.2379. found (ESI(−), [M−H]) 518.2365.

Workup

  1. washFlash chromatography eluted with 9:1 DCM

Sources & evidence

ORD record
ord-f754643fecfc42fbb47d871716083d7c
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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