N-cyclopropyl-4-fluorobenzamide → HCID 66716834, compound

HRID 1184511Notes

Reaction equation

HRID 1184511 reaction equation
[CH:1]1([NH:4][C:5](=[O:13])[C:6]2[CH:11]=[CH:10][C:9](F)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[CH3:14][CH:15]1[O:20][C:19]2[CH:21]=[CH:22][C:23]([O:25][CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:24][C:18]=2[NH:17][C:16]1=[O:32]>>[CH:1]1([NH:4][C:5](=[O:13])[C:6]2[CH:11]=[CH:10][C:9]([N:29]3[CH2:30][CH2:31][CH:26]([O:25][C:23]4[CH:22]=[CH:21][C:19]5[O:20][CH:15]([CH3:14])[C:16](=[O:32])[NH:17][C:18]=5[CH:24]=4)[CH2:27][CH2:28]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 4088729N-cyclopropyl-4-fluorobenzamideHCID 66716991HCID 66716991, compound

Product 1

HCID 66716834HCID 66716834, compoundYield 35.5%

Procedure

Using N-cyclopropyl-4-fluorobenzamide as the alkylating agent, the reaction with 394E was carried out as described for 395 providing the title compound as a tan solid (0.0308 g, 35.5% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.50-0.57 (m, 2H) 0.62-0.70 (m, 2H) 1.35-1.43 (m, 3H) 1.59-1.73 (m, 2H) 1.92-2.05 (m, 2 H) 2.80 (tq, J=7.34, 3.95 Hz, 1H) 3.11-3.22 (m, 2H) 3.56-3.69 (m, 2H) 4.38-4.49 (m, 1 H) 4.54-4.62 (m, 1H) 6.50 (d, J=2.78 Hz, 1H) 6.57 (dd, J=8.84, 2.78 Hz, 1H) 6.88 (d, J=8.84 Hz, 1H) 6.96 (d, J=9.09 Hz, 2H) 7.70 (d, J=8.84 Hz, 2H) 8.14 (d, J=4.29 Hz, 1H) 10.57 (s, 1H). ESI-MS: m/z 422.3 (M+H)+.

Sources & evidence

ORD record
ord-973a87115e51450ca99ed357e79ff4c3
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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