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 1754196Notes

Reaction equation

HRID 1754196 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-483c2d2759ed4a3f8aadb1dbd1a5df16
Source dataset
uspto-grants-2015_10
Patent number
US09169224B2

Reaction notes

Loading…