Dimethylformamide dimethyl acetal → HCID 25094556, compound

HRID 2039790Notes

Reaction equation

[Br-].[C:2]12([CH2:12][NH:13][C:14]([C:16]3[C:17]([CH3:33])=[N+:18]([CH2:22][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=4)=[O:24])[CH:19]=[CH:20][CH:21]=3)=[O:15])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH3:34]OC(OC)N(C)C>CN(C=O)C>[C:2]12([CH2:12][NH:13][C:14]([C:16]3[C:17]4[N:18]([C:22]([C:23](=[O:24])[C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=5)=[CH:34][CH:33]=4)[CH:19]=[CH:20][CH:21]=3)=[O:15])[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([CH2:5]3)[CH2:11]1)[CH2:9]2

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3-[(adamantan-1-ylmethyl)carbamoyl]-1-[2-(3-cyanophenyl)-2-oxoethyl]-2-methylpyridinium bromide (400 mg, 0.81 mmol) and N,N-dimethylformamide dimethyl acetal (0.22 mL, 1.62 mmol) in DMF (2.0 mL) is stirred at 110° C. for 3 h. The mixture is concentrated in vacuo and purified by column chromatography (gradient from CH2Cl2 to 10% EtOAc/CH2Cl2) to give the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.91 (1H, d), 8.53 (1H, t), 8.15 (1H, m), 8.05 (2H, m), 7.74 (1H, t), 7.66 (1H, dd), 7.44 (1H, d), 7.22 (1H, t), 6.95 (1H, d), 3.01 (2H, d), 1.93 (3H, s), 1.63 (6H, m), 1.52 (6H, s). Mass spec. (438.19, M+H).

Workup

concentrationThe mixture is concentrated in vacuo
custompurified by column chromatography (gradient from CH2Cl2 to 10% EtOAc/CH2Cl2)

Sources & evidence

ORD record: ord-73a7ba1a4c454af0b250fd91d6c4361b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580812B2

Reaction notes

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