Diisopropylethylamine → HCID 11606965, compound

HRID 912904Notes

Reaction equation

HRID 912904 reaction equation
[Br:1][C:2]1[C:3]([C:27]([F:30])([F:29])[F:28])=[CH:4][C:5]2[N:9]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16]4[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:12][CH2:11]3)[NH:7][C:6]=2[CH:26]=1.C(N(CC)C(C)C)(C)C.[CH3:40][Si:41]([CH3:48])([CH3:47])[CH2:42][CH2:43][O:44][CH2:45]Cl>ClCCl>[Br:1][C:2]1[C:3]([C:27]([F:30])([F:28])[F:29])=[CH:4][C:5]2[N:9]([CH2:45][O:44][CH2:43][CH2:42][Si:41]([CH3:48])([CH3:47])[CH3:40])[C:8]([N:10]3[CH2:11][CH2:12][N:13]([C:16]4[C:21]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:14][CH2:15]3)=[N:7][C:6]=2[CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178506059HCID 178506059, compound

Product 1

HCID 11606965HCID 11606965, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-5-trifluoromethyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1H-benzoimidazole (203 mg, 0.41 mmol, Example 89 g) in dichloromethane (6 mL) was added N,N-diisopropylethylamine (148 mg, 1.15 mmol) followed by 2-(trimethylsilyl)ethoxymethyl chloride (94 mg, 0.57 mmol, Aldrich). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with EtOAc/hexane (1:3) to afford the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 624 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with EtOAc/hexane (1:3)

Sources & evidence

ORD record
ord-df56482348ae446fbfda2e152a6058a3
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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