Chloride → HCID 23652719, compound

HRID 1094494Notes

Reaction equation

HRID 1094494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH2:21][C:22]4[CH:27]=[C:26](O)[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[Cl-].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:45]>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH2:21][C:22]4[CH:27]=[C:26]([Cl:45])[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30]

Participants

6

Reactant 4

HCID 312ChlorideHCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178522149HCID 178522149, compound

Product 1

HCID 23652719HCID 23652719, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 200 mg (0.453 mMol) 6-(6-hydroxy-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide in 15 ml CH3CN, 165.7 mg (1.0 mMol) tetrmethylammonium chloride, 127 μl (1.0 mMol) N,N-dimethylaniline and 0.55 ml (6.0 mMol) POCl3 are added. The mixture is heated up to 75° C. for 1 h, cooled to rt and poured into 30 g ice. After 1 h of vigorous stirring, the title compound can be filtered off and washed with 6 ml CH3CN/H2O 1:2: MS: [M+1]+=460/462; HPLC: tRet=16.5.

Workup

  1. temperaturecooled to rt
  2. filtrationthe title compound can be filtered off
  3. washwashed with 6 ml CH3CN/H2O 1:2

Sources & evidence

ORD record
ord-5dc33e0ed5114223af54cf794d8181b3
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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