Acetone → {4-[6-[2-(4-Cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-butyl}-trimethyl-ammonium formate

HRID 1497793Notes

Reaction equation

HRID 1497793 reaction equation
[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:40]=[C:11]2[C:12]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)=[C:13]([CH3:29])[C:14]([C:16]3[N:20]([C:21]4[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=4)[N:19]=[CH:18][CH:17]=3)=[CH:15][N:10]2[N:9]=1.[CH3:42][O:43]S(C1C=CC=CC=1)(=O)=O.[CH3:53]C(C)=[O:55]>>[CH:42]([O-:43])=[O:55].[C:25]([C:24]1[CH:23]=[CH:22][C:21]([N:20]2[C:16]([C:14]3[C:13]([CH3:29])=[C:12]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:37])([F:39])[F:38])[CH:31]=4)[C:11]4[N:10]([N:9]=[C:8]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][N+:2]([CH3:53])([CH3:1])[CH3:41])[N:40]=4)[CH:15]=3)=[CH:17][CH:18]=[N:19]2)=[CH:28][CH:27]=1)#[N:26]

Participants

4

Reactant 3

HCID 180AcetoneHCID 6630Methyl benzenesulfonate2×HCID 730519224-{5-[2-(4-Dimethylamino-butylamino)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

Product 1

HCID 73052391{4-[6-[2-(4-Cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-butyl}-trimethyl-ammonium formate

Conditions

Temperature
55 °C

Procedure

To a solution of 4-{5-[2-(4-dimethylamino-butylamino)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Ex. 30, 44 mg, 0.079 mmol) in acetone (0.4 mL) was added methylbenzenesulfonate (12 μL, 0.087 mmol) at ambient temperature. The reaction mixture was heated at 55° C. under N2 for 2.5 hrs. A further quantity of methylbenzenesulfonate (3.2 μL) was added and the mixture was heated at 55° C. for 1 hr. Once cooled the volatiles were evaporated in vacuo and the residue azeotroped with diethyl ether. The resultant residue was subjected to preparative C18 HPLC, eluting with a gradient of 20-70% MeCN in water (+0.1% formic acid) to give the title compound as a white solid (10 mg).

Workup

  1. temperaturethe mixture was heated at 55° C. for 1 hr
  2. temperatureOnce cooled the volatiles
  3. customwere evaporated in vacuo
  4. customthe residue azeotroped with diethyl ether
  5. washeluting with a gradient of 20-70% MeCN in water (+0.1% formic acid)

Sources & evidence

ORD record
ord-096a2f9c42844d41bf4fd47f5614c8b1
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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