Triethylsilane → HCID 178441787, compound

HRID 2179063Notes

Reaction equation

HRID 2179063 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[C:9](=[N:11][N:12]([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)[N:13]=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[C:9](=[N:11][N:12]([CH2:14][C:15]3[C:16]([C:39]([F:40])([F:41])[F:42])=[N:17][NH:18][CH:19]=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 89586309HCID 89586309, compound

Product 1

HCID 178441787HCID 178441787, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The crude 5-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidine and triethylsilane in TFA was stirred at r.t. for 3 h. The reaction mixture was concentrated in vacuo and purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield the title compound as white solid. MS (m/e): 431.3 (MH+)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. additionThe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-c0bbcc7a926c464ba4e75aeb31a5c088
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

Loading…