Methanesulfonic Acid → HCID 178494018, compound

HRID 1481564Notes

Reaction equation

HRID 1481564 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[NH:31][C:14]3[C:15]([O:29][CH3:30])=[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].[S:32]([OH:36])([CH3:35])(=[O:34])=[O:33]>CCOC(C)=O>[CH3:35][S:32]([OH:36])(=[O:34])=[O:33].[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[NH:31][C:14]3[C:15]([O:29][CH3:30])=[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 6395Methanesulfonic AcidHCID 178494017HCID 178494017, compound

Product 1

HCID 178494018HCID 178494018, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-4-methoxy-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine (9.2 mg, 0.021 mmol, prepared as in STEP A) was dissolved in EtOAc (1 mL) and 0.5 M MsOH in EtOAc (41 μL, 0.021 mmol) was added. The resulting solution was thoroughly mixed and the solvent was removed under reduced pressure to yield 2-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-4-methoxy-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine methanesulfonic acid salt. 1H-NMR (400 MHz, acetone-d6) δ: 7.88 (d, J=8.1 Hz, 1H), 7.74-7.80 (m, 1H), 7.66-7.73 (m, 2H), 7.62 (s, 1H), 7.17 (s, 1H), 4.36 (s, 3H), 4.33 (s, 3H), 2.80 (s, 3H), 1.33 (s, 9H). Mass Spectrum (LCMS, ESI pos.): Calculated for C22H22F3N5O: 430.2 (M+H). Measured: 430.2.

Workup

  1. additionThe resulting solution was thoroughly mixed
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f2dfd01622a7456bbfdd0b8a84e3292d
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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