Cyclopropanecarbonyl chloride → HCID 44540487, compound

HRID 1695767Notes

Reaction equation

HRID 1695767 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([C:13](Cl)=[O:14])[CH2:12][CH2:11]1.[CH3:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[C:25]([NH2:38])[C:26]3[C:30]([CH:31]=2)=[N:29][N:28](C2CCCCO2)[CH:27]=3)[CH:20]=[CH:21][CH:22]=1>C1COCC1>[CH3:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[N:28][NH:29]3)=[C:25]([NH:38][C:13]([CH:10]3[CH2:12][CH2:11]3)=[O:14])[CH:24]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 58255733HCID 58255733, compound

Product 1

HCID 44540487HCID 44540487, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

THF (1 ml), DIPEA (0.142 ml, 0.813 mmol) and cyclopropanecarbonyl chloride (34 mg, 0.325 mmol) were added to 6-(3-methylphenyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (50 mg, 0.163 mmol) and the reaction was stirred at RT for 1 h. The solvent was evaporated under a stream of nitrogen and 2 M sodium hydroxide (aq) (3 ml) was added and the reaction stirred for 1 h. DCM (3 ml) was added and the reaction stirred for a further 30 mins. The organic layer was passed through a hydrophobic frit and the aqueous layer extracted with DCM. The combined organic layers were concentrated. The residue was dissolved in MeOH (2 ml) and 4 M HCl in 1,4-dioxane (2 ml) was added. The reaction was stirred for 1 h then the solvent was removed in vacuo. The residue was purified by MDAP (Method A) then freeze dried to give title compound, 17 mg.

Workup

  1. customThe solvent was evaporated under a stream of nitrogen and 2 M sodium hydroxide (aq) (3 ml)
  2. additionwas added
  3. stirringthe reaction stirred for 1 h
  4. additionDCM (3 ml) was added
  5. stirringthe reaction stirred for a further 30 mins
  6. extractionthe aqueous layer extracted with DCM
  7. concentrationThe combined organic layers were concentrated
  8. dissolutionThe residue was dissolved in MeOH (2 ml)
  9. addition4 M HCl in 1,4-dioxane (2 ml) was added
  10. stirringThe reaction was stirred for 1 h
  11. customthe solvent was removed in vacuo
  12. customThe residue was purified by MDAP (Method A)
  13. customthen freeze dried

Sources & evidence

ORD record
ord-0d51b98c85dd487380c26e799886c55f
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

Loading…