2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 9868229, compound

HRID 227622Notes

Reaction equation

HRID 227622 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[N:29]=[C:30]=[O:31]>ClCCl>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:30]([NH:29][C:20]4[CH:21]=[C:22]([C:25]([F:26])([F:28])[F:27])[CH:23]=[CH:24][C:19]=4[F:18])=[O:31])=[CH:7][CH:6]=3)=[CH:9][S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 250237745-(4-Aminophenyl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 9868229HCID 9868229, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of Example 58D (0.04 g, 0.165 mmol) in dichloromethane (3 mL) under nitrogen was cooled to 0° C., treated with 1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene (0.024 mL, 0.165 mmol), and stirred overnight while gradually warming to room temperature. The suspension was filtered and the filter cake was dried in a vacuum oven to provide 0.056 g of the desired product. MS(ESI(+)) m/e 448 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.40 (s, 1H); 8.98 (d, J=2.7 Hz, 1H); 8.63 (dd, J=7.2 Hz, 2.1 Hz, 1H); 8.35 (s, 1H); 7.63 (d, J=8.7 Hz, 2H); 7.55-7.39 (m, 5H).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filter cake was dried in a vacuum oven

Sources & evidence

ORD record
ord-0997b45ad839495ca1e44a0b54f5424d
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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