2-Methoxyethanol → HCID 18617857, compound

HRID 1264308Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[C:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][CH2:20][NH:21][C:22](=[O:36])[C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31](Cl)[N:30]=4)=[CH:25][CH:24]=3)[CH:17]=2)[NH:12][CH:11]=1)#[N:9]>CS(C)=O>[C:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][CH2:20][NH:21][C:22](=[O:36])[C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([O:5][CH2:4][CH2:3][O:2][CH3:1])[N:30]=4)=[CH:25][CH:24]=3)[CH:17]=2)[NH:12][CH:11]=1)#[N:9]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-methoxyethanol (0.118 mL, 1.50 mmoles) in DMSO (5 mL) was added sodium hydride (Aldrich, 60% dispersion, 0.0720 g, 1.80 mmoles), followed by stirring until H2 evolution ceased (15 minutes). One milliliter of this alkoxide stock solution was added to N-[2-(3-Cyano-1H-indol-5-yl)-ethyl]-4-[2-chloropyrimidin-4-yl]benzamide (0.147 g, 0.249 mmoles, reference example 1az), followed by heating (60° C.). After two hours, another 0.5 mL of the alkoxide stock solution was added. After two more hours, the reaction was quenched with water (40 mL) and the resulting precipitate collected by filtration. The precipitate was washed with water and CH2Cl2 and dried under vacuum to give the product as a white solid. MS (ion spray) m/z 442 (M+H)+.

Workup

custom(15 minutes)
customAfter two more hours, the reaction was quenched with water (40 mL)
filtrationthe resulting precipitate collected by filtration
washThe precipitate was washed with water and CH2Cl2
customdried under vacuum

Sources & evidence

ORD record: ord-4385da7a1dae4331a2cfb2a4db7227cf
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541505B1

Reaction notes

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