Sodium Methoxide → HCID 178493218, compound

HRID 518685Notes

Reaction equation

HRID 518685 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=1.[CH3:24][O-:25].[Na+]>C1COCC1>[CH:18]([NH:17][C:15]([C@H:12]1[CH2:13][CH2:14][C@@H:9]([NH:8][C:6]2[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=[C:2]([O:25][CH3:24])[CH:7]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178457831HCID 178457831, compound

Product 1

HCID 178493218HCID 178493218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-bath cooled suspension of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (400 mg, 1.174 mmol) in THF (2.3 mL) was added sodium methoxide (25 wt. % in MeOH (0.859 mL, 3.76 mmol)). The mixture was stirred in an ice bath for 1 minute. The ice bath was removed and the reaction was stirred for 30 minutes. The mixture was diluted with 10% IPA/DCM (5 mL) and washed with saturated aqueous NaHCO3 (1 mL). The layers were separated, and the organic layer was dried with Na2SO4 and the mixture purified via flash chromatography using a linear gradient of 0% to 5% of 1% NH4OH in MeOH in DCM. The title compound was collected as a yellow solid (289 mg, 73%).

Workup

  1. temperatureTo an ice-bath cooled
  2. customThe ice bath was removed
  3. stirringthe reaction was stirred for 30 minutes
  4. additionThe mixture was diluted with 10% IPA/DCM (5 mL)
  5. washwashed with saturated aqueous NaHCO3 (1 mL)
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried with Na2SO4
  8. customthe mixture purified via flash chromatography
  9. customThe title compound was collected as a yellow solid (289 mg, 73%)

Sources & evidence

ORD record
ord-895d963b53be477bbf661a5b765921a2
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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