Hydrochloric Acid → HCID 59375149, compound

HRID 1811102Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:23]=2[CH3:38])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]([O:19]CC)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].[OH-].[Na+].Cl>C(O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29](=[O:37])[C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[C:23]=2[CH3:38])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 92.5 °C

Procedure

A suspension of ethyl 8-carbamoyl-5-(3-(4-fluorobenzamido)-2-methylphenyl)-9H-carbazole-2-carboxylate (Intermediate 3-100, 1.63 g, 3.20 mmol) in ethanol (12 mL) was treated with 1 M aqueous sodium hydroxide (1.5 mL, 1.500 mmol), forming a yellow suspension which was heated at 90-95° C. for 30 min. The mixture was cooled to rt and acidified with 1 M hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to provide 8-carbamoyl-5-(3-(4-fluorobenzamido)-2-methylphenyl)-9H-carbazole-2-carboxylic acid as an off-white solid (1.496 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 12.76 (br. s., 1 H) 11.84 (s, 1 H) 10.15 (s, 1 H) 8.38 (s, 1 H) 8.24 (br. s., 1 H) 8.03-8.13 (m, 3 H) 7.56 (br. s., 1 H) 7.46-7.54 (m, 2 H) 7.42 (t, J=7.7 Hz, 1 H) 7.35 (t, J=9.0 Hz, 2 H) 7.23 (dd, J=7.5, 1.3 Hz, 1 H) 7.04 (d, J=7.5 Hz, 1 H) 7.01 (d, J=8.3 Hz, 1 H) 1.88 (s, 3 H). Mass spectrum m/z 482.1 (M+H)+.

Workup

customforming a yellow suspension which
temperatureThe mixture was cooled to rt
filtrationThe precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-ee29917f7920486e8745ac7d6d14909e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362065B2

Reaction notes

Loading…