3-(Trifluoromethyl)phenyl isocyanate → HCID 59596411, compound

HRID 2264604Notes

Reaction equation

HRID 2264604 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[N:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([N:27]=[C:28]=[O:29])[CH:24]=[CH:25][CH:26]=1>C1COCC1>[F:19][C:20]([F:30])([F:31])[C:21]1[CH:22]=[C:23]([NH:27][C:28]([N:1]2[C:10]3[C:5](=[CH:6][C:7]([O:11][C:12]4[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[N:13]=4)=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[O:29])[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 59596398HCID 59596398, compound

Product 1

HCID 59596411HCID 59596411, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 242 mg (1 mmol) 4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidin-2-ylamine (Step 29.2) in 5 mL of dry THF are added 205 mg (1.1 mmol) of 3-trifluoromethyl-phenylisocyanate at RT. The solution is stirred for 2 h at RT and then the THF is evaporated. The residue is purified by flash-chromatography on silica gel using dichloromethane/methanol 95:5 as eluent. Fractions with pure compound are pooled and evaporated to give the title compound as an amorphous material: MS: [M+1]+=430; HPLC: CtRet=2.14; TLC (dichloromethane/methanol 95:5): Rf=0.45.

Workup

  1. customthe THF is evaporated
  2. customThe residue is purified by flash-chromatography on silica gel
  3. customevaporated

Sources & evidence

ORD record
ord-06d0fb42549f4d89830ee518ff224603
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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