Hydrochloric Acid → HCID 89618808, compound

HRID 926706Notes

Reaction equation

HRID 926706 reaction equation
O[Li].O.[C:4]([O:8][C:9]([NH:11][C:12]1([C:42]([O:44]C)=[O:43])[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:21]=[N:22][N:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][CH2:32][CH2:31][C@@H:30]4[C:34]4[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=4[F:41])=[CH:25][C:24]=23)=[O:19])[CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl>O.C1COCC1.CO>[C:4]([O:8][C:9]([NH:11][C:12]1([C:42]([OH:44])=[O:43])[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:21]=[N:22][N:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][CH2:32][CH2:31][C@@H:30]4[C:34]4[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=4[F:41])=[CH:25][C:24]=23)=[O:19])[CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 89618779HCID 89618779, compound

Product 1

HCID 89618808HCID 89618808, compoundYield 87.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (43 mg, 1 mmol) in water (2 mL) was added to a stirred solution of (R)-methyl 4-((tert-butoxycarbonyl)amino)-1-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carbonyl)piperidine-4-carboxylate (120 mg, 0.2 mmol) in THF (6 mL), MeOH (2 mL) and water (2 mL) at 20-35° C. The reaction mixture was stirred for 6 h; thereafter it was concentrated under reduced pressure to afford a crude product. The crude product thus obtained was diluted with cold water, acidified with 2N aqueous HCl solution, extracted with ethyl acetate, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 100 mg of the title compound as a pale green solid. MS (ESI): m/z 570.2 (M+H).

Workup

  1. concentrationthereafter it was concentrated under reduced pressure
  2. customto afford a crude product
  3. customThe crude product thus obtained
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d978d9aa566945e78d5bf1eb5f75491b
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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