Methanesulfonic Acid → HCID 178494023, compound

HRID 570270Notes

Reaction equation

HRID 570270 reaction equation
[C:1]([C:5]1[C:6]([Cl:29])=[C:7]([C:11]2[NH:28][C:14]3[C:15]([O:26][CH3:27])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[C:1]([C:5]1[C:6]([Cl:29])=[C:7]([C:11]2[NH:28][C:14]3[C:15]([O:26][CH3:27])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])=[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 6395Methanesulfonic AcidHCID 178494021HCID 178494021, compound

Product 1

HCID 178494023HCID 178494023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-4-methoxy-3H-imidazo[4,5-c]pyridine (159 mg, 0.370 mmol, prepared as described in Example 25) in DCM (10 mL) and treated with methanesulfonic acid (35.6 mg, 0.370 mmol) at room temperature for 1 h. The solution was concentrated in vacuo and the resulting solid was triturated with hexanes, filtered, washed with hexanes, air-dried, and placed under high vacuum for 30 min to yield 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-4-methoxy-3H-imidazo[4,5-c]pyridine methanesulfonic acid salt as a white solid. 1H-NMR (400 MHz, CD3OD) δ: 7.64-7.69 (m, 2H), 7.62-7.64 (m, 1H), 7.50-7.61 (m, 2H), 4.75-4.81 (m, 3H), 4.16 (s, 3H), 2.70 (s, 3H), 1.46 (s, 9H). Mass Spectrum (LCMS, APCI pos.) Calculated for C21H21N5OCl2: 430.1 (M+H), Measured: 430.2.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe resulting solid was triturated with hexanes
  3. filtrationfiltered
  4. washwashed with hexanes
  5. customair-dried

Sources & evidence

ORD record
ord-c3b9d1efd4564f61976cd4e4ba2d6aa4
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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