Methanol → HCID 178473725, compound

HRID 849429Notes

Reaction equation

HRID 849429 reaction equation
[ClH:1].Cl.Cl.[NH:4]1[CH:8]=[C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]4[CH:22]=N[CH:24]=[CH:25][CH:26]=4)=[CH:20][C:15]=3[CH2:14][N:13]([C:27](=[O:32])[C:28](F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)[N:6]=[CH:5]1.B.[CH3:41]O>C1COCC1>[ClH:1].[C:27]([N:13]1[CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[CH:41][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:16]=2[N:10]([CH2:9][C:7]2[N:6]=[CH:5][NH:4][CH:8]=2)[CH2:11][C@H:12]1[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:32])[CH3:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 178478619HCID 178478619, compound

Product 1

HCID 178473725HCID 178473725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound B (150 mg, 0.42 mmol) in THF (10 mL) was added borane (1 M in THF, 3 mL, 3 mmol). The solution was refluxed for 3 h and cooled to room temperature. Methanol (5 mL) was added and the solution was concentrated. 5 N HCl (10 mL) was added and the mixture was refluxed for 4 h, cooled to room temperature, neutralized to pH 6 with 50% NaOH and extracted with methylene chloride (3×50 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and concentrated to yield compound C as a slightly yellow glass (70 mg, 50%). MS (M+H)+ 330.

Workup

  1. temperatureThe solution was refluxed for 3 h
  2. concentrationthe solution was concentrated
  3. addition5 N HCl (10 mL) was added
  4. temperaturethe mixture was refluxed for 4 h
  5. temperaturecooled to room temperature
  6. extractionextracted with methylene chloride (3×50 mL)
  7. washThe combined organic layers were washed with brine (30 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ecdcc7bd5032426dbf294cde03ee341a
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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