Dichloromethane → HCID 178481822, compound

HRID 570248Notes

Reaction equation

HRID 570248 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-5049d636a61a4d38b8054a168ff2f974
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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