Trifluoroacetic acid → HCID 90017353, compound

HRID 1055025Notes

Reaction equation

HRID 1055025 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:40]([F:43])([F:42])[F:41])[C:12]2[N:13]([N:16]=[C:17]([CH2:19][CH2:20][C:21]3[N:25](CC4C=CC(OC)=CC=4)[N:24]=[C:23]([N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[N:22]=3)[N:18]=2)[C:14]=1[CH3:15]>>[Cl:8][C:9]1[CH:10]=[C:11]([C:40]([F:42])([F:41])[F:43])[C:12]2[N:13]([N:16]=[C:17]([CH2:19][CH2:20][C:21]3[NH:25][N:24]=[C:23]([N:35]4[CH2:36][CH2:37][CH2:38][CH2:39]4)[N:22]=3)[N:18]=2)[C:14]=1[CH3:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90017217HCID 90017217, compound

Product 1

HCID 90017353HCID 90017353, compoundYield 40.5%

Procedure

Trifluoroacetic acid (9.87 g, 6.67 ml, 86.5 mmol, Eq: 100) was added to 6-chloro-2-(2-(1-(4-methoxybenzyl)-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-5-methyl-8-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (450 mg, 865 μmol, Eq: 1.00). The mixture was heated under reflux for 4 h and then concentrated to an oil. Water (15 ml) was added and the mixture was alkalized by addition of sodium bicarbonate. The mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to an oil. The crude product was purified by chromatography (SiO2, methanol ethyl acetate) to afford the product (140 mg, 40.5%) as an off white solid. MS: m/z=400.2 (M+H+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationconcentrated to an oil
  4. additionWater (15 ml) was added
  5. additionthe mixture was alkalized by addition of sodium bicarbonate
  6. extractionThe mixture was extracted with dichloromethane
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated to an oil
  9. customThe crude product was purified by chromatography (SiO2, methanol ethyl acetate)

Sources & evidence

ORD record
ord-714e5a8b67f141fda190590fef7b1ab6
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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