Hantzsch ester → HCID 90409680, compound

HRID 2177592Notes

Reaction equation

HRID 2177592 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[N:7]1[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:9]=[N:8]1.[Cl:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].CCOC(C1CC(C(OCC)=O)=C(C)NC=1C)=O>C1COCC1>[Cl:16][C:17]1[C:25]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([N:12]1[CH:13]=[CH:14][C:15]2[N:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)[N:8]=[N:9][C:10]=2[CH2:11]1)=[O:20]

Participants

5

Reactant 3

HCID 70849Hantzsch esterHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 90409694HCID 90409694, compound2×

Product 1

HCID 90409680HCID 90409680, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-pyrazin-2-yl-1H-[1,2,3]triazolo[4,5-c]pyridine (Intermediate 40) (50 mg, 0.25 mmol) in THF (2.0 mL) was treated with 2-chloro-3-(trifluoromethyl)benzoyl chloride (67 mg, 0.28 mmol) and stirred for 5 minutes. The reaction was treated with Hantzsch Ester (269 mg, 1.0 mmol) and heated to 80° C. in sealed tube for 90 min. Reaction was concentrated and purified on 16 g SiO2 with 0-50% EtOAc/hexanes to yield 87 mg (85% yield) MS (ESI): mass calcd. for C17H10ClF3N6O, 406.1. m/z found, 407.1 [M+H]+.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. custompurified on 16 g SiO2 with 0-50% EtOAc/hexanes
  4. customto yield 87 mg (85% yield)

Sources & evidence

ORD record
ord-770afc6f51ac407f95d02b914a968696
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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