2-[(4-Quinolin-3-ylmethyl-piperazine-1-carbonyl)-amino]-benzoic acid methyl ester → 2-[(4-Quinolin-3-ylmethyl-piperazine-1-carbonyl)-amino]-benzoic acid

HRID 40592Notes

Reaction equation

HRID 40592 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:21]=[N:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][CH2:14]1)=[O:12]>C1COCC1>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[C:20]([CH2:19][N:16]2[CH2:15][CH2:14][N:13]([C:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:30])=[O:2])=[O:12])[CH2:18][CH2:17]2)[CH:21]=1

Participants

3

Reactant 1

HCID 116111202-[(4-Quinolin-3-ylmethyl-piperazine-1-carbonyl)-amino]-benzoic acid methyl ester

Product 1

HCID 578808802-[(4-Quinolin-3-ylmethyl-piperazine-1-carbonyl)-amino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(4-quinolin-3-ylmethyl-piperazine-1-carbonyl)-amino]-benzoic acid methyl ester (26 mg) in THF (0.5 mL) under N2 was added potassium trimethyl silanoate (9 mg) in one portion and the mixture was stirred at rt for 14 h. The mixture was concentrated to give the title compound as a white amorphous solid (22 mg). 1H NMR (400 MHz, CD3OD): 8.81 (d, J=2.1 Hz, 1H), 8.23-8.21 (m, 1H), 8.14 (dd, J=8.4, 0.9 Hz, 1H), 7.96-7.93 (m, 1H), 7.91 (dd, J=7.9, 1.6 Hz, 1H), 7.88-7.85 (m, 1H), 7.68 (ddd, J=8.4, 6.9, 1.4 Hz, 1H), 7.54 (ddd, J=8.1, 7.0, 1.1 Hz, 1H), 7.19-7.23 (m, 1H), 6.81-6.85 (m, 1H), 3.71 (s, 2H), 3.51-3.54 (m, 4H), 2.49-2.51 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-ac63cbac4f634fc79d74b3f803e73d39
Source dataset
uspto-grants-2013_09
Patent number
US08530476B2

Reaction notes

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