HCID 67326745, compound → HCID 178510193, compound

HRID 1500777Notes

Reaction equation

HRID 1500777 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[C:9]([C:11]1[CH:16]=[CH:15][N:14]2[N:17]=[CH:18][C:19]([C:20]3[N:25]=[C:24](N[C@@H]4CCCN(C(OC(C)(C)C)=O)C4)[CH:23]=[CH:22][N:21]=3)=[C:13]2[CH:12]=1)#[N:10]>CN(C=O)C>[OH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([NH:1][C:22]2[CH:23]=[CH:24][N:25]=[C:20]([C:19]3[CH:18]=[N:17][N:14]4[CH:15]=[CH:16][C:11]([C:9]#[N:10])=[CH:12][C:13]=34)[N:21]=2)[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 67326745HCID 67326745, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178510193HCID 178510193, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trans-4-aminocyclohexanol (85 mg, 0.74 mmol) was added to a solution of 3-(4-(1H-benzo[d][1,2,3]triazol-1-yloxy)pyrimidin-2-yl)pyrazolo[1,5-a]pyridine-5-carbonitrile (byproduct of Preparation 7a, 105 mg, 0.30 mmol) in N,N′-dimethylformamide (3 mL) and the mixture was stirred at ambient temperature overnight. The solvent was then evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent evaporated. The crude product was purified by flash chromatography (dichloromethane to 9:1 dichloromethane/methanol) to give the title compound (66 mg, 67%) as a yellow solid.

Workup

  1. customThe solvent was then evaporated
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. customThe crude product was purified by flash chromatography (dichloromethane to 9:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-e23118c7a60e49f695e07740c09b3083
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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