5-Isocyanatoisoquinoline → N-isoquinolin-5-yl-N'-[7-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-yl]urea

HRID 2092154Notes

Reaction equation

[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)=[C:2]=[O:3].[F:14][C:15]([F:28])([F:27])[C:16]1[CH:25]=[C:24]2[C:19]([CH:20]([NH2:26])[CH2:21][CH2:22][O:23]2)=[CH:18][CH:17]=1>>[CH:9]1[C:10]2[C:5](=[C:4]([NH:1][C:2]([NH:26][CH:20]3[C:19]4[C:24](=[CH:25][C:16]([C:15]([F:28])([F:14])[F:27])=[CH:17][CH:18]=4)[O:23][CH2:22][CH2:21]3)=[O:3])[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

Reactant 2

HCID 115863575-Isocyanatoisoquinoline

HCID 468354217-(Trifluoromethyl)chroman-4-amine

Product 1

HCID 53251332N-isoquinolin-5-yl-N'-[7-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-yl]ureaYield 23%

Procedure

3 ml of the 5-isocyanato-isoquinoline solution was added to the product of Example 4D (49 mg, 0.3 mmol) and stirred at ambient temperature overnight, and the precipitate formed was collected by filtration and washed with diethyl ether to give 23 mg of the title compound (23% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.28 (s, 1H), 8.63 (s, 1H), 8.55 (d, J=6.0 Hz, 1H), 8.32 (m, 1H), 7.90 (d, J=6.0 Hz, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.60 (m, 2H), 7.30-7.12 (m, 3H), 5.02 (m, 1H), 4.42-4.20 (m, 2H), 2.30-2.00 (m, 2H). MS (ESI) m/e 388 (M+H)+. Calcd. For C20H16N3O2F3.0.2; H2O: C, 62.01; H, 4.16; N, 10.85. Found: C, 61.29; H, 3.94; N, 10.64.

Workup

customthe precipitate formed
filtrationwas collected by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-9dc617c97dc44ee59396e6b572542abd
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440691B2

Reaction notes

Loading…