Cyclohexylamine → HCID 25241920, compound

HRID 1852533Notes

Reaction equation

HRID 1852533 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:9]1[N:14]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[N:16]2)[C:12]([Cl:24])=[CH:11][N:10]=1>C1COCC1>[N:15]1([C:13]2[C:12]([Cl:24])=[CH:11][N:10]=[C:9]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 25241964HCID 25241964, compound

Product 1

HCID 25241920HCID 25241920, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexylamine (0.21 mL, 1.88 mmol) was added in portions to a solution of 1-(2,5-dichloro-pyrimidin-4-yl)-1H-benzotriazole (250 mg, 0.94 mmol) in THF (30 mL) at RT under nitrogen atmosphere. The resultant colorless solution was stirred at RT for 4 hours. TEA (2.82 mmol) was then added and the reaction mixture was stirred at RT overnight. The mixture was partitioned between water (50 mL) and EtOAc (50 mL). The organic layer was separated, washed twice with water (50 mL) and once with brine (50 mL), then dried over Na2SO4, filtered and evaporated under reduced pressure to give an off-white solid. This crude material was purified via flash chromatography (toluene/EtOAc, 98/2) to afford 162 mg (53% yield) of (4-benzotriazol-1-yl-5-chloro-pyrimidin-2-yl)-cyclohexyl-amine as an off-white solid. MS: 329.14 (M+1)+, 301.14 ((M+1)+−28).

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. customThe mixture was partitioned between water (50 mL) and EtOAc (50 mL)
  3. customThe organic layer was separated
  4. washwashed twice with water (50 mL) and once with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an off-white solid
  9. customThis crude material was purified via flash chromatography (toluene/EtOAc, 98/2)

Sources & evidence

ORD record
ord-aad022192ca94a889345a591ca20975e
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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