Methanol → HCID 178511734, compound

HRID 707380Notes

Reaction equation

HRID 707380 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=[CH:13]2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.CO>C(Cl)Cl.CCOC(C)=O>[N:12]1([C@H:10]2[CH2:9][C@H:8]([NH2:7])[CH2:11]2)[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 178454099HCID 178454099, compound

Product 1

HCID 178511734HCID 178511734, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of tert-butyl(trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (294 mg, 1.02 mmol) in DCM (2.0 ml) was added trifluoroacetic acid, 99% (760 μl, 10.2 mmol). The reaction mixture was stirred at room temperature under N2 for 1 h. The solvent was evaporated and the residue was triturated with DCM three times, redissolved in DCM, and then treated with solid NaHCO3. The solid was filtered off and the filtrate concentrated in vacuo. The crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 100% EtOAc in hexane, then 15% MeOH in EtOAc, to provide trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutanamine (75 mg, 0.401 mmol, 39.2% yield) as light-yellow oil. ESI (M+1) 188.0.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with DCM three times
  3. dissolutionredissolved in DCM
  4. additiontreated with solid NaHCO3
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  8. washeluting with a gradient of 0% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-516deb8a39714743b52a3f018d74afbd
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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