2,2,2-Trifluoroethanol → HCID 57786083, compound

HRID 1399181Notes

Reaction equation

HRID 1399181 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:24]([CH:26]2[CH2:28][CH2:27]2)[OH:25])=[CH:4][CH:3]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[F:60][C:61]([F:65])([F:64])[CH2:62]O>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:24]([CH:26]2[CH2:28][CH2:27]2)[O:25][CH2:62][C:61]([F:65])([F:64])[F:60])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57786231HCID 57786231, compound

Product 1

HCID 57786083HCID 57786083, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of [9-chloro-1-(6-methoxy-2-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl](cyclopropyl)methanol (111.5 mg, 0.280 mmol) in tetrahydrofuran (2.8 mL) was added 1,1′-(azodicarbonyl)dipiperidine (141.1 mg, 0.559 mmol) and tributylphosphine (139.3 μL, 0.559 mmol). After 10 min, to the mixture was added 2,2,2-trifluoroethanol (204.0 μL, 2.800 mmol). The reaction mixture was stirred at 60° C. for 2 hrs. The mixture was concentrated. To the residue was added diethyl ether and the precipitate was removed by filtration. The residue was purified by silica gel column chromatography eluting with a 0-50% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless powder (92.4 mg, 0.192 mmol, 69%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionTo the residue was added diethyl ether
  3. customthe precipitate was removed by filtration
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with a 0-50% ethyl acetate/n-hexane gradient mixture
  6. customThe resulting solid was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-d150b0c19e7546ddb95e5b7e84e746d3
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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