Methyl benzenesulfonate → {3-[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]-propyl}-trimethyl-ammonium benzenesulfonate

HRID 1497792Notes

Reaction equation

HRID 1497792 reaction equation
[CH3:1][N:2]([CH3:40])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[N:39]=[C:10]2[C:11]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)=[C:12]([CH3:28])[C:13]([C:15]3[N:19]([C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=4)[N:18]=[CH:17][CH:16]=3)=[CH:14][N:9]2[N:8]=1.[CH3:41][O:42][S:43]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(=[O:45])=[O:44]>CC(C)=O>[C:46]1([S:43]([O-:45])(=[O:44])=[O:42])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[C:24]([C:23]1[CH:22]=[CH:21][C:20]([N:19]2[C:15]([C:13]3[C:12]([CH3:28])=[C:11]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[CH:30]=4)[C:10]4[N:9]([N:8]=[C:7]([NH:6][CH2:5][CH2:4][CH2:3][N+:2]([CH3:41])([CH3:1])[CH3:40])[N:39]=4)[CH:14]=3)=[CH:16][CH:17]=[N:18]2)=[CH:27][CH:26]=1)#[N:25]

Participants

4

Reactant 2

HCID 6630Methyl benzenesulfonateHCID 730519204-{5-[2-(3-Dimethylamino-propylamino)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

Product 1

HCID 73052080{3-[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]-propyl}-trimethyl-ammonium benzenesulfonateYield 89.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-{5-[2-(3-dimethylamino-propylamino)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Ex. 28, 55 mg, 0.10 mmol) in acetone (0.44 mL) was added methylbenzenesulfonate (15 μL, 0.11 mmol) at ambient temperature. The reaction mixture was heated 55° C. for 1.5 hrs. The cooled reaction mixture was concentrated in vacuo to give a clear colorless oil. The oil thus obtained was triturated in diethyl ether and the resultant solid taken up in minimal EtOAc and Et2O added until a white solid formed. The precipitate was collected by filtration, washed with Et2O and dried in vacuo to yield the title compound as a white solid (64 mg).

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customto give a clear colorless oil
  4. customThe oil thus obtained
  5. customwas triturated in diethyl ether
  6. additionEt2O added until a white solid
  7. customformed
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with Et2O
  10. customdried in vacuo

Sources & evidence

ORD record
ord-ff8a2e09e4314ed18a7442eb7c809a05
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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