Hydrochloric Acid → HCID 66605036, compound

HRID 2410801Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]([C:26]([O:28]C)=[O:27])[C:10]3[NH:11][C:12]4[CH:13]=[C:14]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH:15]=[CH:16][C:17]=4[C:18]=3[N:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+].Cl>C1COCC1>[CH:23]([O:22][C:20]([C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[N:19]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=[C:9]([C:26]([OH:28])=[O:27])[C:10]=3[NH:11][C:12]=2[CH:13]=1)=[O:21])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 7-isopropyl 4-methyl 2-phenyl-5H-pyrido[3,2-b]indole-4,7-dicarboxylate (380 mg, 0.978 mmol) in a mixture of THF (5.6 mL), MeOH (1.9 mL) and 1 N aqueous sodium hydroxide solution (2.0 mL, 2.0 mmol) was stirred at 25° C. for 15 min. The reaction was treated with 1 N aqueous HCl (0.52 mL) and the organic solvents were removed. The residue was diluted with water and acidified to about pH 3.0 with 1 N aqueous HCl to give an yellow gel-like precipitate. This was chilled in an ice bath and the precipitate was collected by filtration, washed with water and dried to leave impure 7-(isopropoxycarbonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylic acid (395 mg). MS (ESI) m/z 375.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.88 (1H, s), 8.35-8.50 (3H, m), 8.25 (2H, d, J=7.94 Hz), 7.83-7.96 (1H, m), 7.56 (2H, t, J=7.78 Hz), 7.46 (1H, t, J=7.17 Hz), 5.22 (1H, quin, J=6.26 Hz), 1.40 (6H, d, J=6.10 Hz).

Workup

customthe organic solvents were removed
additionThe residue was diluted with water
customto give an yellow gel-like precipitate
temperatureThis was chilled in an ice bath
filtrationthe precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-59bdf921315341baabffbf5df136566c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

Loading…