Acetic Acid → HCID 66997420, compound

HRID 2363627Notes

Reaction equation

HRID 2363627 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[N:8]=[C:7]([N:9]2[CH2:13][C@@H:12]3[C@@H:14]([NH2:17])[CH2:15][CH2:16][C@@H:11]3[CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[CH3:20][C:21]([CH3:23])=O.C(O)(=O)C.C([BH3-])#N>ClCCl>[CH:21]([NH:17][C@@H:14]1[C@@H:12]2[C@@H:11]([CH2:10][N:9]([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:18])[F:19])[N:8]=3)[CH2:13]2)[CH2:16][CH2:15]1)([CH3:23])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 498716Cyano-borohydrideHCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66997420HCID 66997420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3aR,4S,6aS)-2-(6-(Trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine from Example 264 Step A (44 mg, 0.162 mmol) and acetone (14.13 mg, 0.243 mmol) were combined in dichloromethane (0.5 mL). Acetic acid (0.5 mL) was added. The reaction mixture was stirred at ambient temperature for 30 minutes, then PS-cyanoborohydride (146 mg, 0.324 mmol) was added. After 18 hours, the reaction mixture was filtered and the solvent removed under a stream of nitrogen. The crude material was applied to a 4 g silica gel cartridge and purified with a gradient of 1-10% methanol in (2 N ammonia)/dichloromethane to give to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.57-7.52 (m, 1H), 6.99 (d, J=7.2, 1H), 6.55 (d, J=8.6, 1H), 3.62-3.54 (m, 1H), 3.54-3.45 (m, 2H), 3.25 (dd, J=10.7, 4.3, 1H), 3.03 (dd, J=11.8, 5.9, 1H), 2.83 (dt, J=12.4, 6.2, 1H), 2.76-2.67 (m, 1H), 2.49-2.41 (m, 1H), 2.02-1.92 (m, 2H), 1.45-1.29 (m, 3H), 1.06 (d, J=6.2, 3H), 1.03 (d, J=6.2, 3H); MS (ESI+) m/z 314 (M+H)+.

Workup

  1. waitAfter 18 hours
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent removed under a stream of nitrogen
  4. custompurified with a gradient of 1-10% methanol in (2 N ammonia)/dichloromethane
  5. customto give

Sources & evidence

ORD record
ord-8321b4b365e8403fb17745855d271e32
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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