6-chloro-4-phenyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one → 6-chloro-4-cyclopropyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 19707Notes

Reaction equation

HRID 19707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:5]2([C:22]1[CH:27]=[CH:26]C=CC=1)[C:18]([F:21])([F:20])[F:19].ClC1C=C2C(=CC=1)NC(=O)N(CC(F)(F)F)C2(O)C(F)(F)F.C1([Mg]Br)CC1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:5]2([CH:22]1[CH2:27][CH2:26]1)[C:18]([F:21])([F:20])[F:19]

Participants

4

Reactant 3

HCID 118540726-chloro-4-phenyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-oneHCID 593466016-Chloro-4-hydroxy-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydro-quinazolin-2(1H)-oneHCID 178418630HCID 178418630, compound

Product 1

HCID 118543326-chloro-4-cyclopropyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Procedure

Utilizing the general procedure outlined for 6-chloro-4-phenyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one, 6-chloro-4-hydroxy-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (217 mg, 0.62 mmol) was reacted with 0.5 M cyclopropyl magnesium bromide (4.9 ml, 2.5 mmol) to afford 6-chloro-4-cyclopropyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one as an oil. 1H NMR (CD3OD, 400 MHz) δ 7.89 (d, J=2.0 Hz, 1H), 7.36 (dd, J=2.4 and 8.6 Hz), 1H), 6.91 (dd, J=1.6 Hz and 7.6 Hz, 1H), 4.74 (m, 1H), 4.52 (m, 1H), 1.50 (m, 1H), 1.26 (m, 2H), 1.15 (m, 1H), 1.02 (m, 1H). Exact Mass (Electrospray, M+H) Calc'd, 373.0537; Found, 373.0541.

Sources & evidence

ORD record
ord-7967780b2c13469aa8d613d6c2eba334
Source dataset
uspto-grants-2010_06
Patent number
US07745452B2

Reaction notes

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