Triethylamine → 6-Fluoro-3-(4-triisopropylsilanyloxy-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1402124Notes

Reaction equation

HRID 1402124 reaction equation
FC(F)(F)S([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])(=O)=O.[F:19][C:20]1[CH:21]=[CH:22][C:23]2[N:24]([C:26]([N:29]3[CH2:34][CH2:33][CH:32](O)[CH2:31][CH2:30]3)=[N:27][N:28]=2)[CH:25]=1.CCN(CC)CC>CN(C=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]2[N:24]([C:26]([N:29]3[CH2:34][CH2:33][CH:32]([O:6][Si:7]([CH:8]([CH3:9])[CH3:10])([CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:15])[CH3:16])[CH2:31][CH2:30]3)=[N:27][N:28]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 2724529Triisopropylsilyl trifluoromethanesulfonate2×HCID 86686988HCID 86686988, compound

Product 1

HCID 866869896-Fluoro-3-(4-triisopropylsilanyloxy-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triisopropylsilyl trifluoromethanesulfonate (395 mg, 1.29 mmol) was added dropwise to a solution of Intermediate 24c (254 mg, 1.07 mmol) and Et3N (0.20 mL, 1.40 mmol) in DMF (3 mL) at RT under N2. The mixture was stirred for 1 h then Et3N (0.10 ml, 0.70 mmol) and triisopropylsilyl trifluoromethanesulfonate (200 mg, 0.65 mmol) were added sequentially, and the mixture stirred for 1 h. The solvent was evaporated, the residue applied to an SCX-2 cartridge and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo left the title compound (339 mg, 80%). LCMS (Method 1): Rt 4.74 min, m/z 393 [MH+].

Workup

  1. stirringthe mixture stirred for 1 h
  2. customThe solvent was evaporated
  3. washwashed with MeOH
  4. washThe product was eluted with 2M NH3 in MeOH
  5. concentrationconcentration in vacuo
  6. waitleft the title compound (339 mg, 80%)

Sources & evidence

ORD record
ord-1b196a387ea645d4ad2de64f3ee65403
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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