Dichloromethane → HCID 178481822, compound

HRID 1191231Notes

Reaction equation

HRID 1191231 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[NH:30][C:14]3[C:15]([Cl:29])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:32]>CO>[C:1]([C:5]1[C:6]([Cl:32])=[C:7]([C:11]2[NH:30][C:14]3[C:15]([Cl:29])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:27])([F:28])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178481819HCID 178481819, compound2×

Product 1

HCID 178481822HCID 178481822, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-4-chloro-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine (101 mg, 0.232 mmol, Compound #74 freebase prepared according to Example 16, STEPS A, B and C) in DCM (2 mL) was treated with SO2Cl2 (28.3 μL, 0.348 mmol) and the resulting mixture was stirred at room temperature for 14 h. The resulting mixture was then diluted with MeOH (3 mL) and the solvent was removed under reduced pressure. The residue was chromatographed on a 25-g SiO2 pre-packed column eluting with 0:1-3:7 EtOAc/hexanes to yield 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-4-chloro-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine. 1H-NMR (400 MHz, CD3OD) δ: 7.84 (d, J=7.8 Hz, 1H), 7.69-7.76 (m, 1H), 7.68 (s, 1H), 7.62-7.67 (m, 1H), 7.59 (d, J=7.6 Hz, 1H), 4.14 (s, 3H), 1.45 (s, 9H). Mass Spectrum (LCMS, ESI pos.): Calculated for C21H18Cl2F3N5: 468.1 (M+H); Measured: 468.1.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on a 25-g SiO2 pre-packed column
  3. washeluting with 0:1-3:7 EtOAc/hexanes

Sources & evidence

ORD record
ord-d9d793ef19fc4a29b2b018206305c6d4
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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