Water → HCID 59718937, compound

HRID 1852535Notes

Reaction equation

HRID 1852535 reaction equation
CS[C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[N:10]2)[CH:6]=[CH:5][N:4]=1.ClNC(=O)CCC(N)=O.O.[CH:28]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN1C(=O)CCC1>[N:9]1([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([NH:34][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[N:8]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 15238416N-chlorosuccinamideHCID 59718927HCID 59718927, compound

Product 1

HCID 59718937HCID 59718937, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazole (376 mg, 1.5 mmol) in 4 mL of NMP were added N-chlorosuccinamide (250 mg, 1.9 mmol) and 0.5 mL of water. The mixture was placed in an oil bath at 130° C. for 5-10 minutes, cyclohexylamine (450 mg, 5 mmol) was then added and the reaction mixture was stirred in an oil bath at 130° C. for 30 minutes. The cooled reaction mixture was partitioned between water (40 mL) and EtOAc (40 mL). The organic layer was separated and washed twice with water (40 mL), then dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude residue was purified by flash chromatography and recrystallized from CH2Cl2/EtOAc to give (4-benzotriazol-1-yl-pyrimidin-2-yl)-cyclohexyl-amine as a white short-needle crystalline solid (255 mg, 56% yield). mp=202.0-204.0° C.; MS=295 (M+H)+.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between water (40 mL) and EtOAc (40 mL)
  3. customThe organic layer was separated
  4. washwashed twice with water (40 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe crude residue was purified by flash chromatography
  9. customrecrystallized from CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-0d56c95c00ea4f56a847ebc6e4c7462e
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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