Water → HCID 66767058, compound

HRID 2195513Notes

Reaction equation

HRID 2195513 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[NH:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[N:14]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[N:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](Cl)(=[O:33])[CH3:32].C([O-])([O-])=O.[K+].[K+].O>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[N:18]([CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1)[C:31](=[O:33])[CH3:32])[N:14]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[N:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 66767251HCID 66767251, compound

Product 1

HCID 66767058HCID 66767058, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(benzyloxy)-1-(tetrahydro-2H-pyran-2-yl)-N-(tetrahydro-2H-pyran-4-yl)-1H-indazol-6-amine (1.87 g, 4.59 mmol) in THF (30 mL) is added acetyl chloride (0.39 mL, 5.48 mmol) and K2CO3 (760 mg, 5.50 mmol). After the reaction mixture is heated to reflux for 30 min, H2O (20 mL) and EtOAc (30 mL) are added. The organic phase is separated, washed with saturated aqueous NH4Cl, dried and concentrated to give the product (1.7 g, 82.4% yield). MS (m/z): 450.2 (M+H).

Workup

  1. temperatureAfter the reaction mixture is heated
  2. temperatureto reflux for 30 min
  3. customThe organic phase is separated
  4. washwashed with saturated aqueous NH4Cl
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-055e4135098f4713a82db90de0712a2a
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

Loading…