Sodium Hydroxide → HCID 44540029, compound

HRID 1695758Notes

Reaction equation

HRID 1695758 reaction equation
O1CCCCC1[N:7]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C4CCCCO4)[CH:18]=3)[CH:12]=[C:13]2[NH2:16])=[N:8]1.CCN(C(C)C)C(C)C.[CH:39]1([C:45](Cl)=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.[OH-].[Na+]>C(Cl)Cl>[OH:23][C:19]1[CH:18]=[C:17]([C:11]2[CH:12]=[C:13]3[C:14]([CH:15]=[N:7][NH:16]3)=[C:9]([NH:8][C:45]([CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:46])[CH:10]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 75938Cyclohexanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 58255762HCID 58255762, compound

Product 1

HCID 44540029HCID 44540029, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Tetrahydro-2H-pyran-2-yl)-6-[3-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine (50 mg, 0.127 mmol) was dissolved in DCM (1 ml) and DIPEA (0.111 ml, 0.635 mmol) and cyclohexanecarbonyl chloride (45 mg, 0.254 mmol) were added. The reaction was stirred at RT for 1 h. 2 M Sodium hydroxide (aq) (2 ml) was added and the reaction stirred at RT for 1 h, before the organic layer was passed through a hydrophobic frit. The aqueous layer was washed several times with DCM, which was passed through a hydrophobic frit. The combined organic layers were evaporated under a stream of nitrogen. The residue was dissolved in MeOH (2 ml) and 4 M HCl in dioxane was added (2 ml). The reaction was stirred at RT for 1 h. The solvent was removed under a stream of nitrogen and the residue was dissolved in DMSO:MeOH (1:1, v/v) and purified by MDAP (Method B). The residue was dissolved in 1,4-dioxane:water and freeze dried to produce the title compound.

Workup

  1. stirringthe reaction stirred at RT for 1 h, before the organic layer
  2. washThe aqueous layer was washed several times with DCM, which
  3. customThe combined organic layers were evaporated under a stream of nitrogen
  4. dissolutionThe residue was dissolved in MeOH (2 ml)
  5. addition4 M HCl in dioxane was added (2 ml)
  6. stirringThe reaction was stirred at RT for 1 h
  7. customThe solvent was removed under a stream of nitrogen
  8. dissolutionthe residue was dissolved in DMSO:MeOH (1:1
  9. customv/v) and purified by MDAP (Method B)
  10. dissolutionThe residue was dissolved in 1,4-dioxane
  11. dry with materialwater and freeze dried

Sources & evidence

ORD record
ord-b677472f6067438ab8ad820c010b3851
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

Loading…