Methanesulfonic Acid → HCID 178480781, compound

HRID 1481585Notes

Reaction equation

HRID 1481585 reaction equation
[C:1]([C:5]1[C:6]([Cl:37])=[C:7]([C:11]2[NH:36][C:14]3[C:15]([N:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)=[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].[CH3:38][S:39]([OH:42])(=[O:41])=[O:40]>C(Cl)Cl>[CH3:38][S:39]([OH:42])(=[O:41])=[O:40].[C:1]([C:5]1[C:6]([Cl:37])=[C:7]([C:11]2[NH:36][C:14]3[C:15]([N:29]4[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]4)=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:26])([F:27])[F:28])=[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 178480780HCID 178480780, compound

Product 1

HCID 178480781HCID 178480781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-4-(4-methyl-piperazin-1-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine (158 mg, 0.297 mmol, prepared as described in the previous step) in DCM (10 mL) was treated with methanesulfonic acid (19.2 μL, 0.297 mmol) at room temperature for 1 h. The resulting mixture was concentrated in vacuo, triturated with hexanes, and filtered. The solid was air-dried and placed under high vacuum for 30 min to yield 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-4-(4-methyl-piperazin-1-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine methanesulfonic acid salt as a tan solid. 1H-NMR (400 MHz, CD3OD) δ: 7.83 (d, J=8.3 Hz, 1H), 7.68-7.74 (m, 1H), 7.58-7.65 (m, 2H), 7.20 (s, 1H), 5.52 (d, J=13.1 Hz, 2H), 4.12 (s, 3H), 3.64 (d, J=11.6 Hz, 2H), 3.45-3.58 (m, 2H), 3.26 (br. s., 2H), 2.96 (s, 3H), 2.69 (s, 4H), 1.45 (s, 9H). Mass Spectrum (LCMS, APCI pos.): Calculated for C26H29ClF3N7: 532.2 (M+H). Measured: 532.2.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customtriturated with hexanes
  3. filtrationfiltered
  4. customThe solid was air-dried

Sources & evidence

ORD record
ord-d9f40505d7f244d59dbfebfdafb84fde
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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