Methanol → HCID 71226920, compound

HRID 2369991Notes

Reaction equation

HRID 2369991 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#N)=[CH:17][CH:16]=2)[CH2:10]1.B(F)(F)F.CC[O:29][CH2:30]C.C[OH:33]>>[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]([O:29][CH3:30])=[O:33])=[CH:17][CH:16]=2)[CH2:10]1

Participants

4

Reactant 3

HCID 887MethanolHCID 8000Boron trifluoride etherate2×HCID 71226426HCID 71226426, compound

Product 1

HCID 71226920HCID 71226920, compoundYield 100%

Procedure

To a solution of 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (70 mg, 0.235 mmol) in MeOH (1 mL) at was added BF3.OEt2 (0.2 mL, 1.578 mmol) at rt. The reaction was stirred at reflux for 16 h. LC/MS showed only ˜22% of the desired products formed. More BF3.OEt2 (100 μL, 0.789 mmol) was added. The reaction was stirred at reflux for another 6 days. The reaction mixture was concentrated. The residue was diluted with EtOAc, washed with saturated aq NaHCO3, saturated aq NaCl solution. The organic extracts were concentrated under vacuum to give the crude product methyl 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzoate (78 mg, 0.235 mmol, 100% yield). The product was used without further purification.

Workup

  1. temperatureat reflux for 16 h
  2. customformed
  3. stirringThe reaction was stirred
  4. temperatureat reflux for another 6 days
  5. concentrationThe reaction mixture was concentrated
  6. additionThe residue was diluted with EtOAc
  7. washwashed with saturated aq NaHCO3, saturated aq NaCl solution
  8. concentrationThe organic extracts were concentrated under vacuum

Sources & evidence

ORD record
ord-acb390f25d7747b6af40e5a01415cc02
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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