Cyclopropanecarbonyl chloride → N-[6-(4-Hydroxyphenyl)-1H-indazol-4-yl]cyclopropanecarboxamide

HRID 1695768Notes

Reaction equation

HRID 1695768 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([C:13](Cl)=[O:14])[CH2:12][CH2:11]1.O1CCCCC1[N:22]1[CH:30]=[C:29]2[C:24]([CH:25]=[C:26]([C:32]3[CH:37]=[CH:36][C:35]([O:38]C4CCCCO4)=[CH:34][CH:33]=3)[CH:27]=[C:28]2[NH2:31])=[N:23]1>C(Cl)Cl>[OH:38][C:35]1[CH:34]=[CH:33][C:32]([C:26]2[CH:25]=[C:24]3[C:29]([CH:30]=[N:22][NH:23]3)=[C:28]([NH:31][C:13]([CH:10]3[CH2:12][CH2:11]3)=[O:14])[CH:27]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 582558372-(Tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine

Product 1

HCID 135927892N-[6-(4-Hydroxyphenyl)-1H-indazol-4-yl]cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (82 mg, 0.635 mmol) and cyclopropanecarbonyl chloride (15 mg, 0.14 mmol) were added to 2-(tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine (50 mg, 0.127 mmol) in DCM (1 ml) and the reaction was stirred for 1 h. The solvent was removed under a stream of nitrogen. The residue was dissolved in MeOH (2 ml), 4 M HCl in 1,4-dioxane (2 ml) was added and the reaction was stirred for 1 h. The solvent was removed in vacuo. The residue was purified by MDAP (Method B), dried under a stream of nitrogen then freeze dried to give the title compound, 17 mg.

Workup

  1. customThe solvent was removed under a stream of nitrogen
  2. dissolutionThe residue was dissolved in MeOH (2 ml)
  3. addition4 M HCl in 1,4-dioxane (2 ml) was added
  4. stirringthe reaction was stirred for 1 h
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by MDAP (Method B)
  7. customdried under a stream of nitrogen
  8. customthen freeze dried

Sources & evidence

ORD record
ord-62552b56bcb04ce18c13f3ad4378ecf4
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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