Lithium hydroxide, monohydrate → HCID 67994795, compound

HRID 2361438Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[C:37](=[O:38])[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[CH:29]3)[C:23]=2[CH3:39])=[C:8]2[C:12]=1[NH:11][C:10]1[CH:13]=[N:14][C:15]([C:17]([O:19]CC)=[O:18])=[CH:16][C:9]2=1)(=[O:3])[NH2:2].O.[OH-].[Li+]>C1COCC1.C(O)C.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[C:37](=[O:38])[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[CH:29]3)[C:23]=2[CH3:39])=[C:8]2[C:12]=1[NH:11][C:10]1[CH:13]=[N:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:9]2=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl 8-carbamoyl-5-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (0.26 g, 0.502 mmol) and lithium hydroxide monohydrate (0.070 g, 1.757 mmol) in THF-ethanol-water (3:1:1, 20.10 mL) was stirred at room temperature overnight. After 18 h, residual starting material was observed by LCMS. The mixture was heated at 50° C. for 2 h, then cooled to room temperature and concentrated. The residue was suspended in water and treated with 1 M aqueous HCl (to pH 1-2). The precipitate was collected by filtration, washed with water and dried to provide the desired product as a pale yellow solid (0.205 g, 76%). LCMS (M+H)+ m/z 490.1.

Workup

temperaturecooled to room temperature
concentrationconcentrated
additiontreated with 1 M aqueous HCl (to pH 1-2)
filtrationThe precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-1dac341d8d2347059b2686b3ce8488d3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

Loading…