Water → HCID 21865194, compound

HRID 858992Notes

Reaction equation

HRID 858992 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH2:22])[CH:10]=2)=[CH:5][CH:4]=1.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28].CCN(CC)CC.O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:22][C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 21865318HCID 21865318, compound

Product 1

HCID 21865194HCID 21865194, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-phenylamine, (Example 26), (0.33 g, 1.0 mmol), butyryl chloride (0.15 mL, 1.5 mmol, Aldrich), and 4-dimethylaminopyridine (0.006 g, 0.05 mmol, Aldrich) in CH2Cl2 (5 mL) was added Et3N (0.21 mL, 1.5 mmol, Aldrich). The mixture was stirred for 30 min, diluted with hexanes (10 ml) and treated with H2O (2 mL). The resulting solids were filtered, washed with H2O and hexanes, and dried in vacuum for 16 h at room temperature to give the title compound as a white powder. Mp: 112° C., MS (ESI, pos. ion) m/z: 402 (M+1).

Workup

  1. filtrationThe resulting solids were filtered
  2. washwashed with H2O and hexanes
  3. customdried in vacuum for 16 h at room temperature

Sources & evidence

ORD record
ord-ced9c68fc1bb490a9608ce211faf7722
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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