1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 178521887, compound

HRID 2203275Notes

Reaction equation

HRID 2203275 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:22][N:12]3[C:13](=[O:21])[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34]>C1COCC1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[CH2:22][N:12]4[C:13](=[O:21])[NH:14][C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=5[C:11]4=[N:10][CH2:9]3)=[CH:4][CH:3]=2)=[O:32])=[CH:26][C:25]=1[C:33]([F:34])([F:35])[F:36]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 178507413HCID 178507413, compound

Product 1

HCID 178521887HCID 178521887, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-aminophenyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,2-c]quinazolin-6-one (20.2 mg, 0.069 mmol) in 1.6 mL THF was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (16.8 mg, 0.076 mmol) and the reaction stirred at rt. After 45 min, the reaction was briefly warmed to approximately 50° C. and then allowed to cool to rt. After 1.5 hours the stirring was stopped and the reaction left to stand at rt overnight. Then using a stream of nitrogen and gentle heating, the THF was evaporated to 1 mL, let mixture stand for 30 minutes, then filtered and rinsed with 50% EtOAc in hexane to give the title compound as an off-white solid (20.9 mg, 59%). 1H NMR (DMSO-d6) δ: 10.69 (br. s, 1H), 9.14 (br. s, 1H), 8.82 (br. s, 1H), 8.10 (d, J=2.3 Hz, 1H), 7.97-7.99 (m, 1H), 7.59-7.65 (m, 2H), 7.42-7.45 (m, 3H), 7.26 (d, J=8.8 Hz, 2H), 7.05-7.08 (m, 1H), 7.01 (d, J=7.9 Hz, 1H), 4.20-4.24 (m, 1H), 3.70-3.75 (m, 1H), 3.52-3.59 (m, 2H), 2.94-3.01 (m, 1H).

Workup

  1. temperaturethe reaction was briefly warmed to approximately 50° C.
  2. temperatureto cool to rt
  3. waitAfter 1.5 hours the stirring was stopped
  4. waitthe reaction left
  5. waitto stand at rt overnight
  6. customthe THF was evaporated to 1 mL
  7. waitstand for 30 minutes
  8. filtrationfiltered
  9. washrinsed with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-8060e5b876224acc8baaf1b3584f41f2
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

Loading…