2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 178521888, compound

HRID 2203273Notes

Reaction equation

HRID 2203273 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.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=1[N:34]=[C:35]=[O:36]>C1COCC1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=1[NH:34][C:35]([NH: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)=[O:36]

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 178507413HCID 178507413, compound

Product 1

HCID 178521888HCID 178521888, compoundYield 85%

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 (6.1 mg, 0.021 mmol) in 0.7 mL THF was added 2-fluoro-5-(trifluoromethyl)phenyl isocyanate (0.0033 mL, 0.023 mmol) and the reaction stirred at rt. After 1 hour the reaction was quenched with MeOH, evaporated, triturated with hot EtOAc, hexane added, and the solid filtered to give the title compound as a white solid (8.8 mg, 85%). 1H NMR (Acetone-d6) δ: 9.54 (br. s, 1H), 8.77-8.82 (m, 1H), 8.63 (br. s, 1H), 8.33 (d, J=3.2 Hz, 1H), 8.09-8.13 (m, 1H), 7.54-7.59 (m, 2H), 7.29-7.48 (m, 5H), 7.06-7.12 (m, 2H), 4.34-4.42 (m, 1H), 3.79-3.87 (m, 1H), 3.54-3.69 (m, 2H), 3.00-3.11 (m, 1H).

Workup

  1. customAfter 1 hour the reaction was quenched with MeOH
  2. customevaporated
  3. customtriturated with hot EtOAc, hexane
  4. additionadded
  5. filtrationthe solid filtered

Sources & evidence

ORD record
ord-c701520b06364d7fba06f0f4a8651fda
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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