Dimethylformamide → HCID 90112476, compound

HRID 1509066Notes

Reaction equation

HRID 1509066 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([C:18]2[N:19]=[C:20](OS(C(F)(F)F)(=O)=O)[C:21]3[S:27](=[O:29])(=[O:28])[CH2:26][CH2:25][CH2:24][C:22]=3[N:23]=2)[CH:15]=[CH:16][CH:17]=1.CN(C=O)C>O>[Cl:11][C:12]1[CH:13]=[C:14]([C:18]2[N:19]=[C:20]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=3)[C:21]3[S:27](=[O:29])(=[O:28])[CH2:26][CH2:25][CH2:24][C:22]=3[N:23]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 770004-AminophenylacetonitrileHCID 90111594HCID 90111594, compound

Product 1

HCID 90112476HCID 90112476, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

An 8-mL vial was charged with 2-(4-aminophenyl)acetonitrile (30 mg, 0.23 mmol, 2 eq.), [2-(3-Chlorophenyl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]trifluoromethanesulfonate (50 mg, 0.112 mmol, 1. eq.) and DMF (0.5 ml). The resulting mixture was stirred at 70° C. overnight. After cooling to room temperature, water was added to the mixture (5 ml). The precipitate was collected by filtration and washed with water (10 ml). After drying, the crude product was purified by chromatography on silica gel using dichloromethane as eluent to give the title compound (18 mg, 38% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water (10 ml)
  4. customAfter drying
  5. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a74f89e2cfda4d86b463b3df0733e5d6
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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