Triethylsilane → HCID 178441788, compound

HRID 400925Notes

Reaction equation

HRID 400925 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:43]2[CH2:47][CH2:46][C:45]([F:49])([F:48])[CH2:44]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[C:16]([C:39]([F:42])([F:41])[F:40])=[N:17][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:19]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[C:1]([C:5]1[N:6]=[C:7]([N:43]2[CH2:47][CH2:46][C:45]([F:48])([F:49])[CH2:44]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[C:16]([C:39]([F:40])([F:41])[F:42])=[N:17][NH:18][CH:19]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 86683333HCID 86683333, compound

Product 1

HCID 178441788HCID 178441788, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of crude 5-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine, triethylsilane in TFA was stirred at room temperature for 3 h, concentrated and subjected to purification with preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. After evaporation of the product containing fractions the title compound was isolated as white solid. MS (m/e): 431.3 (MH+).

Workup

  1. concentrationconcentrated
  2. customsubjected to purification with preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. customAfter evaporation of the product
  6. additioncontaining fractions the title compound
  7. customwas isolated as white solid

Sources & evidence

ORD record
ord-8754521d3fd04a369d77a7aede3bce06
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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