Diisopropylethylamine → HCID 89586134, compound

HRID 2179037Notes

Reaction equation

HRID 2179037 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:14]2[CH2:18][CH2:17][C:16]([F:20])([F:19])[CH2:15]2)[C:8]2[N:13]=[N:12][NH:11][C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])=[O:24].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([C:5]1[N:6]=[C:7]([N:14]2[CH2:18][CH2:17][C:16]([F:19])([F:20])[CH2:15]2)[C:8]2[C:9](=[N:11][N:12]([CH2:22][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[O:24])[N:13]=2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27357852-Bromo-2'-chloroacetophenoneHCID 178441789HCID 178441789, compound

Product 1

HCID 89586134HCID 89586134, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (11.6 mg, 41.1 μmol), 2-bromo-1-(2-chlorophenyl)ethanone (11.5 mg, 7.19 μl, 49.3 μmol) and DIPEA (10.6 mg, 14.4 μl, 82.2 μmol) were combined with DCM (250 μl) to give a light yellow solution. The reaction mixture was stirred at r.t. for 4 h 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 1.9 mg (11%) of the title compound as yellow gum. MS (m/e): 435.3 (MH+).

Workup

  1. customto give a light yellow solution
  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-c5163df242b045369c8b73d25a421498
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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