Triethylamine → 6,8-dichloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[3,4-d][1,3]oxazin-4-one

HRID 887701

Reaction equation

HRID 887701 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13](Cl)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:20][C:21]1[C:29]([Cl:30])=[N:28][C:27]([Cl:31])=[CH:26][C:22]=1[C:23](O)=[O:24].C(N(CC)CC)C.CS(Cl)(=O)=O>C(#N)C>[Cl:31][C:27]1[N:28]=[C:29]([Cl:30])[C:21]2[N:20]=[C:13]([C:12]3[N:8]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=4)[N:9]=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=3)[O:14][C:23](=[O:24])[C:22]=2[CH:26]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl ChlorideHCID 593555213-Amino-2,6-dichloroisonicotinic acid

Product 1

HCID 593555246,8-dichloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[3,4-d][1,3]oxazin-4-oneYield 96.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Trifluoromethyl-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid chloride (example 2, step 3) (242 mg) was added to a mixture of 3-amino-2,6-dichloroisonicotinic acid (example 1, step 8) (190 mg) in acetonitrile (3 mL). The mixture was stirred for 5 minutes at room temperature and triethylamine (220 μL) was added and stirred for 20 minutes, before a second portion of triethylamine (220 μL) was added. After the mixture was stirred for further 20 minutes at room temperature, methanesulfonyl chloride (70 μL) was added. After stirring for 2 hours at room temperature, the formed precipitate was filtered off, washed carefully with water and MTB-ether and dried in vacuum to afford 350 mg of the title compound of the formula

Workup

  1. additionwas added
  2. stirringAfter the mixture was stirred for further 20 minutes at room temperature
  3. stirringAfter stirring for 2 hours at room temperature
  4. filtrationthe formed precipitate was filtered off
  5. washwashed carefully with water and MTB-ether
  6. customdried in vacuum

Sources & evidence

ORD record
ord-656341aedc0b496abd1d564216721c1d
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Linked notes

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