Hydrochloric Acid → HCID 178478935, compound

HRID 1191230Notes

Reaction equation

HRID 1191230 reaction equation
[C:1]([C:5]1[C:9]([C:10]#[N:11])=[C:8]([C:12]2[NH:31][C:15]3[C:16]([Cl:30])=[N:17][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[CH:19][C:14]=3[N:13]=2)[N:7]([CH3:32])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CCOCC>CCOC(C)=O>[ClH:30].[C:1]([C:5]1[C:9]([C:10]#[N:11])=[C:8]([C:12]2[NH:31][C:15]3[C:16]([Cl:30])=[N:17][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:28])([F:29])[F:27])=[CH:19][C:14]=3[N:13]=2)[N:7]([CH3:32])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178481828HCID 178481828, compound

Product 1

HCID 178478935HCID 178478935, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-tert-Butyl-5-[4-chloro-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1-methyl-1H-pyrazole-4-carbonitrile (111 mg, 0.241 mmol, prepared as in the previous step) in EtOAc (1 mL) was treated with 1 M HCl in Et2O solution (0.241 mL, 0.241 mmol). The resulting mixture was thoroughly mixed and the solvent was removed under reduced pressure to yield 3-tert-butyl-5-[4-chloro-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1-methyl-1H-pyrazole-4-carbonitrile hydrochloride. 1H-NMR (400 MHz, DMSO-d6) δ: 7.90 (d, J=7.6 Hz, 1H), 7.84 (s, 1H), 7.80 (t, J=7.3 Hz, 1H), 7.71 (t, J=7.6 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 4.11 (s, 3H), 1.44 (s, 9H). Mass Spectrum (LCMS, ESI pos.): Calculated for C22H18ClF3N6: 459.1 (M+H); Measured: 459.2.

Workup

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

Sources & evidence

ORD record
ord-742d46501293469a844f0f66d58116a2
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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