HCID 117842934, compound → HCID 117842917, compound

HRID 2209164Notes

Reaction equation

HRID 2209164 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([O:30][C@@H:31]([C@@H:33]3[CH2:37][C:36](=[O:38])[NH:35][CH2:34]3)[CH3:32])=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)=[N:15][CH:16]=3)=[CH:10][C:5]=2[N:4]=[CH:3]1>C(O)(C(F)(F)F)=O>[CH3:1][N:2]1[C:6]2[C:7]([O:30][C@@H:31]([C@H:33]3[CH2:34][NH:35][C:36](=[O:38])[CH2:37]3)[CH3:32])=[N:8][C:9]([C:11]3[CH:16]=[N:15][C:14]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

3

Reactant 1

HCID 117842934HCID 117842934, compound

Product 1

HCID 117842917HCID 117842917, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl 4-(5-(3-methyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)pyridin-2-yl)piperazine-1-carboxylate (76%, 265 mg, 0.39 mmol)) was dissolved in TFA (4.4 mL) and stirred at room temperature for 15 mins. The reaction was cooled to OC, neutralized to a pH of 7 using satd. sodium bicarbonate, extracted with 30 mL of dichloromethane to remove impurities and then 25% methanol/dichloromethane (300 mL), dried, filtered, concentrated to provide the (R)-4-((R)-1-((3-methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (130 mg, 80% for two steps).

Workup

  1. temperatureThe reaction was cooled to OC
  2. extractionsodium bicarbonate, extracted with 30 mL of dichloromethane
  3. customto remove impurities
  4. dry with material25% methanol/dichloromethane (300 mL), dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-02b1aa3187904e34acc11d1135d42766
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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