Hydrochloric Acid → 4-{5-[2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-3-methanesulfonyl-benzonitrile

HRID 1497803Notes

Reaction equation

HRID 1497803 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([CH3:30])=[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C:10]2[N:11]([N:13]=[C:14]([NH:16]C(=O)C)[N:15]=2)[CH:12]=1)=O.[NH:32]([C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][C:35]=1[S:42]([CH3:45])(=[O:44])=[O:43])[NH2:33].Cl.CCOC(C)=O>C(O)CCC>[NH2:16][C:14]1[N:15]=[C:10]2[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)=[C:8]([CH3:30])[C:7]([C:5]3[N:32]([C:34]4[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][C:35]=4[S:42]([CH3:45])(=[O:44])=[O:43])[N:33]=[CH:3][CH:4]=3)=[CH:12][N:11]2[N:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 867081104-Hydrazino-3-methanesulfonyl-benzonitrileHCID 86708112N-[6-(3-Dimethylamino-acryloyl)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

Product 1

HCID 730523944-{5-[2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-3-methanesulfonyl-benzonitrileYield 3.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-[6-(3-Dimethylamino-acryloyl)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide (Int. 25, 247 mg, 0.573 mmol) and 4-hydrazino-3-methanesulfonyl-benzonitrile (Int. 22, 181 mg, 0.86 mmol) were heated at 100° C. in a mixture of n-butanol (10 mL) and conc. HCl (0.3 mL) for 1.5 h. EtOAc was added and the mixture was concentrated in vacuo. The resultant residue was purified by preparative C18 HPLC, eluting with a gradient of 40-90% MeCN in water (+0.1% formic acid) to give the title compound as a yellow solid (10 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe resultant residue was purified by preparative C18 HPLC
  3. washeluting with a gradient of 40-90% MeCN in water (+0.1% formic acid)

Sources & evidence

ORD record
ord-54916e2fcfa54d0c907b2a7af955603f
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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