Hydrochloric Acid → HCID 66767290, compound

HRID 1662003Notes

Reaction equation

HRID 1662003 reaction equation
C1(C(=[N:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][C:30]=3[F:31])[N:27]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[N:26]=[CH:25]4)=[C:17]([F:38])[CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.Cl.CCOC(C)=O>C1COCC1.O>[F:38][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][C:30]=1[F:31])[N:27]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1)[N:26]=[CH:25]2)[NH2:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86638475HCID 86638475, compound

Product 1

HCID 66767290HCID 66767290, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(diphenylmethylene-3-fluoro-4-(6fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yloxy)aniline (1.45 g, 2.85 mmol) in THF (30 mL) and water (5 mL) is added 1N aqueous HCl (5.69 mL, 5.69 mmol). The reaction is stirred at RT for 2 hours. EtOAc is added and the mixture is washed with saturated aqueous NaHCO3 solution, saturated aqueous sodium chloride, dried over Na2SO4, filtered and evaporated. The residue is purified by chromatography eluting with DCM then EtOAc:hexane (1:1) to offer the desired product as a pale gel (0.53 g, 54% yield). MS (m/z): 346 (M+H).

Workup

  1. washthe mixture is washed with saturated aqueous NaHCO3 solution, saturated aqueous sodium chloride
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography
  6. washeluting with DCM

Sources & evidence

ORD record
ord-758ae78ddb3f490583efdfff6e1e43ff
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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