2,2,2-Trifluoroethyl trifluoromethanesulfonate → tert-butyl (+/-)-6-methoxy-6-methyl-4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 57987Notes

Reaction equation

HRID 57987 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[CH:10][C:9]3[CH:12]=[N:13][N:14]([C:15]4[N:20]=[C:19]([N:21]5[CH2:27][C:26]([O:29][CH3:30])([CH3:28])[CH2:25][N:24]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][CH2:22]5)[CH:18]=[CH:17][CH:16]=4)[C:8]=3[CH:7]=2)[CH:3]=[N:2]1.FC(F)(F)S(O[CH2:44][C:45]([F:48])([F:47])[F:46])(=O)=O>CN(C=O)C>[CH3:30][O:29][C:26]1([CH3:28])[CH2:25][N:24]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][CH2:22][N:21]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([N:14]3[C:8]4[CH:7]=[C:6]([C:4]5[CH:5]=[N:1][N:2]([CH2:44][C:45]([F:48])([F:47])[F:46])[CH:3]=5)[N:11]=[CH:10][C:9]=4[CH:12]=[N:13]3)[N:20]=2)[CH2:27]1

Participants

4

Reactant 2

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 86707170HCID 86707170, compound

Product 1

HCID 86707171tert-butyl (+/-)-6-methoxy-6-methyl-4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-methoxy-6-methyl-1,4-diazepane-1-carboxylate (265 mg, 0.53 mmol) in DMF (15 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (610 mg, 2.63 mmol). The mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine, extracted with DCM (100 mL×3), and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford tert-butyl(±)-6-methoxy-6-methyl-4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as a white solid (264 mg, 85%). MS (ESI) m/z: 587 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with brine
  2. extractionextracted with DCM (100 mL×3)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-050c7b9c0ee747da8a687ad1dd262331
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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