Trifluoroacetic acid → (2R,3S,5R)-5-[2,6-Dihydro-2-(methylsulfonyl)pyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2-(2,4,5-trifluorophenyl)-2H-pyran-3-amine

HRID 1477321Notes

Reaction equation

HRID 1477321 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@@H:10]1[C@@H:15]([NH:16]C(=O)OC(C)(C)C)[CH2:14][C@@H:13]([N:24]2[CH2:31][C:30]3[C:26](=[N:27][N:28]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:29]=3)[CH2:25]2)[CH2:12][O:11]1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@@H:10]1[C@@H:15]([NH2:16])[CH2:14][C@@H:13]([N:24]2[CH2:31][C:30]3[C:26](=[N:27][N:28]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:29]=3)[CH2:25]2)[CH2:12][O:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86641696HCID 86641696, compound

Product 1

HCID 46209242(2R,3S,5R)-5-[2,6-Dihydro-2-(methylsulfonyl)pyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2-(2,4,5-trifluorophenyl)-2H-pyran-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate obtained in Step A above (379 mg, 0.734 mmol) in dichloromethane (20 mL) was treated with trifluoroacetic acid (10 mL) at room temperature. After 2 h, the reaction was concentrated and the crude material was purified on a silica gel column (40S Biotage™) eluting with in 0-2% methanol, containing 10% NH4OH, in dichloromethane to give the title compound as a white solid. 1H NMR (500 MHz, CD3OD): δ 1.50 (q, 1H, J=12 Hz); 2.43-2.49 (m, 1H); 2.88 (td, 1H, J=12, 6 Hz); 3.11-3.18 (m, 1H); 3.34 (s, 3H); 3.40 (t, 1H, J=12 Hz); 3.48-3.92 (m, 4H); 4.23-4.28 (m, 2H); 7.14-7.20 (m, 1H); 7.36-7.42 (m, 1H); 7.86 (s, 1H). LC-MS: 417.12 (M+1).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe crude material was purified on a silica gel column (40S Biotage™)
  3. washeluting with in 0-2% methanol
  4. additioncontaining 10% NH4OH

Sources & evidence

ORD record
ord-1d18ad69320e4b2ea5f239302905e871
Source dataset
uspto-grants-2016_08
Patent number
US09403790B2

Reaction notes

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