Pyridine → 2-[5-(3,5-Bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methylbenzo[d][1,3]oxazin-4-one

HRID 1842538Notes

Reaction equation

HRID 1842538 reaction equation
CS(Cl)(=O)=O.[F:6][C:7]([F:34])([F:33])[C:8]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]([CH2:17][C:18]2[CH:19]=[C:20]([C:30](O)=[O:31])[N:21]([C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[N:22]=2)[N:9]=1.N1C=CC=CC=1.[NH2:41][C:42]1[C:51]([CH3:52])=[CH:50][C:49]([Cl:53])=[CH:48][C:43]=1[C:44](NC)=[O:45]>C(#N)C>[F:34][C:7]([F:6])([F:33])[C:8]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]([CH2:17][C:18]2[CH:19]=[C:20]([C:30]3[O:31][C:44](=[O:45])[C:43]4[CH:48]=[C:49]([Cl:53])[CH:50]=[C:51]([CH3:52])[C:42]=4[N:41]=3)[N:21]([C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[N:22]=2)[N:9]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 250682512-Amino-5-Chloro-N,3-DimethylbenzamideHCID 866385275-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylic acid

Product 1

HCID 591730282-[5-(3,5-Bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methylbenzo[d][1,3]oxazin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

Under argon 0.12 ml (1.60 mmol) of methanesulphonyl chloride in 3 ml of acetonitrile are cooled to 0° C. and subsequently a solution of 540 mg (1.228 mmol) of 5-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylic acid in 0.17 ml (2.09 mmol) of pyridine and 6 ml of acetonitrile is added dropwise. The mixture is stirred at this temperature for 15 minutes and then a solution of 228 mg (1.228 mmol) of 2-amino-5-chloro-3,N-dimethylbenzamide in 0.35 ml (4.30 mmol) of pyridine and 6 ml of acetonitrile is added. After a further 15 minutes at 0° C. the mixture is admixed with 0.12 ml (1.60 mmol) of methanesulphonyl chloride and warmed slowly to room temperature overnight. The solvent is removed in vacuo, 15 ml of water are added and the crystals formed are filtered off with suction.

Workup

  1. customThe solvent is removed in vacuo, 15 ml of water
  2. additionare added
  3. customthe crystals formed
  4. filtrationare filtered off with suction

Sources & evidence

ORD record
ord-96a6e6f81dc04e14bda22b6891e4cd1d
Source dataset
uspto-grants-2015_02
Patent number
US08946236B2

Reaction notes

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