Ammonia → 2-(5-dimethylaminomethyl-2-trifluoromethyl-1H-indol-3-yl)-acetamide

HRID 402899Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][N:16]([CH3:18])[CH3:17])[CH:13]=2)[NH:8][C:7]=1[C:19]([F:22])([F:21])[F:20])C.[NH3:24]>CO>[CH3:17][N:16]([CH2:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:19]([F:22])([F:21])[F:20])=[C:6]2[CH2:5][C:4]([NH2:24])=[O:3])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (5-dimethylaminomethyl-2-trifluoromethyl-1H-indol-3-yl)-acetic acid ethyl ester (200 mg, 0.609 mmol) in a mixture of methanol (5 mL) and liquid ammonia (30 mL) is stirred for 6 days in an autoclave at 80° C. After careful evaporation of the ammonia, the remaining solvent is evaporated in vacuo to afford the title compound as a red solid (182 mg, 0.609 mmol, 100%). 1H NMR (400 MHz, DMSO-d6, 298 K): δ=12.18 (bs, 1H), 7.75 (s, 1H), 7.49 (d, J=8.6 Hz, 1H), 7.42 (bs, 1H), 7.35 (d, J=8.6 Hz, 1H), 6.95 (bs, 1H), 3.67 (s, 2H), 3.16 (s, 2H), 2.62 (s, 6H). MS (ES+): 248 (M(C14H17NO3)+H)+. MS (ES+): 300

Workup

customAfter careful evaporation of the ammonia
customthe remaining solvent is evaporated in vacuo

Sources & evidence

ORD record: ord-d8acd519decd431e98bc68ffc1bf2d0f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742132B2

Reaction notes

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