Dichloromethane → N-[(1S,4S,6S)-3-azabicyclo[4.1.0]hept-4-ylmethyl]-5-(trifluoromethyl)-2-pyrazinamine

HRID 1094768Notes

Reaction equation

HRID 1094768 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[N:4]=[CH:5][C:6]([NH:9][CH2:10][C@@H:11]2[CH2:17][C@H:16]3[C@H:14]([CH2:15]3)[CH2:13][N:12]2C(OC(C)(C)C)=O)=[N:7][CH:8]=1.C(Cl)Cl>>[C@H:14]12[CH2:15][C@H:16]1[CH2:17][C@@H:11]([CH2:10][NH:9][C:6]1[CH:5]=[N:4][C:3]([C:2]([F:26])([F:25])[F:1])=[CH:8][N:7]=1)[NH:12][CH2:13]2

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 593960051,1-dimethylethyl (1S,4S,6S)-4-({[5-(trifluoromethyl)-2-pyrazinyl]amino}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

Product 1

HCID 59396007N-[(1S,4S,6S)-3-azabicyclo[4.1.0]hept-4-ylmethyl]-5-(trifluoromethyl)-2-pyrazinamine

Procedure

To a solution of 1,1-dimethylethyl (1S,4S,6S)-4-({[5-(trifluoromethyl)-2-pyrazinyl]amino}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate D30 (100 mg) in DCM (4 ml) TFA (2 ml, 26.0 mmol) was added dropwise. The mixture was left reacting at room temperature for 2 hours. Solvent was evaporated in vacuum and the crude was purified by SCX chromatography using MeOH 100% to MeOH/NH3 2M. It was recovered the title compound D31 (57 mg). UPLC: (Acid Final_QC): rt=0.48 minutes, peaks observed: 273 (M+1). C12H15F3N4 requires 272. 1H NMR (400 MHz, CDCl3). δ ppm 0.22-0.29 (m, 1 H) 0.67-0.76 (m, 1 H) 0.82-0.92 (m, 1 H) 1.02-1.13 (m, 1 H) 1.24-1.35 (m, 1 H) 2.01-2.12 (m, 1 H) 2.63-2.72 (m, 1 H) 2.95-3.06 (m, 1 H) 3.17 (dd, 1 H) 3.26 (d, 1 H) 3.53-3.63 (m, 1 H) 5.96 (br. s., 1 H) 7.91-7.96 (m, 1 H) 8.26-8.31 (m, 1 H).

Workup

  1. waitThe mixture was left
  2. customSolvent was evaporated in vacuum
  3. customthe crude was purified by SCX chromatography
  4. customIt was recovered the title compound D31 (57 mg)
  5. customrt=0.48 minutes, peaks

Sources & evidence

ORD record
ord-6b83bdbc9ffe49cb89ae9ba22f0ab365
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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