Dimethylcarbamoyl Chloride → HCID 46836875, compound

HRID 1520226Notes

Reaction equation

HRID 1520226 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1.N1CCCN2CCCCCC=12.[CH3:30][N:31]([CH3:35])[C:32](Cl)=[O:33]>C1COCC1.O>[CH3:30][N:31]([CH3:35])[C:32]([N:16]1[CH:15]=[C:14]([C:3]2[N:4]=[C:5]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[S:6][C:2]=2[CH3:1])[CH:18]=[N:17]1)=[O:33]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 25138329HCID 25138329, compound

Product 1

HCID 46836875HCID 46836875, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 19: A solution of 5-methyl-4-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-2-amine (0.39 mmol, 100 mg), 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.39 mmol, 58 μL) and dimethylcarbamic chloride (0.39 mmol, 36 μL) in THF (5 mL) was stirred at room temperature during one day. Then, 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.39 mmol, 58 μL) and dimethylcarbamic chloride (0.39 mmol, 36 μL) were added and the mixture was stirred at room temperature during 3 days. The solution was diluted with water (50 mL) and the aqueous layer was extracted twice with DCM. The organic phases were dried over MgSO4, were filtered and were concentrated to afford a beige solid. The crude compound was purified by flash chromatography with silica gel using DCM/MeOH (98:2) as eluent to afford N,N-dimethyl-4-(5-methyl-2-(pyridin-2-ylamino)thiazol-4-yl)-1H-pyrazole-1-carboxamide (0.23 mmol, 76 mg, 60%) as a beige solid.

Workup

  1. extractionthe aqueous layer was extracted twice with DCM
  2. dry with materialThe organic phases were dried over MgSO4
  3. filtrationwere filtered
  4. concentrationwere concentrated
  5. customto afford a beige solid
  6. customThe crude compound was purified by flash chromatography with silica gel

Sources & evidence

ORD record
ord-0cd65a20057e4fd4a659bfb45f81cdc4
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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