Triethylamine → HCID 86692635, compound

HRID 1748685Notes

Reaction equation

HRID 1748685 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].[NH:15]1[CH2:21][CH2:20][CH2:19][CH:18]([C:22]2[N:27]=[CH:26][C:25]([NH:28][C:29]([C:31]3[CH:32]=[N:33][N:34]([C:37]4[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][N:38]=4)[C:35]=3[CH3:36])=[O:30])=[CH:24][C:23]=2[CH3:47])[CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>O1CCCC1.CN(C)C=O>[CH3:8][N:9]([CH3:14])[S:10]([N:15]1[CH2:21][CH2:20][CH2:19][CH:18]([C:22]2[N:27]=[CH:26][C:25]([NH:28][C:29]([C:31]3[CH:32]=[N:33][N:34]([C:37]4[CH:42]=[CH:41][C:40]([C:43]([F:45])([F:44])[F:46])=[CH:39][N:38]=4)[C:35]=3[CH3:36])=[O:30])=[CH:24][C:23]=2[CH3:47])[CH2:17][CH2:16]1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 516892Sodium BicarbonateHCID 86692633HCID 86692633, compound

Product 1

HCID 86692635HCID 86692635, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.16 ml) and dimethylsulfamoyl chloride (157 mg) were added at room temperature to a solution of N-[6-(azepan-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (250 mg) described in Example K66(1) in tetrahydrofuran (5.5 ml) and N,N-dimethylformamide (5.5 ml), and stirred at 60° C. for three hours. After completion of the reaction, the reaction solution was cooled to room temperature, saturated aqueous solution of sodium bicarbonate was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (133 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-bbcd6e80cd7d4f90bbd9d5d86b64816c
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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