Hydrochloric Acid → HCID 86666949, compound

HRID 511031Notes

Reaction equation

HRID 511031 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([NH:11]C(=O)OCC2C=CC=CC=2)[CH3:10])=[C:4]([O:22][CH3:23])[C:3]=1[CH:24]1[CH2:27][N:26]([CH2:28][C:29]([F:32])([F:31])[F:30])[CH2:25]1.[ClH:33].O>CO>[ClH:1].[ClH:33].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([NH2:11])[CH3:10])=[C:4]([O:22][CH3:23])[C:3]=1[CH:24]1[CH2:25][N:26]([CH2:28][C:29]([F:30])([F:32])[F:31])[CH2:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86666951HCID 86666951, compound

Product 1

HCID 86666949HCID 86666949, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl (1-{4,5-dichloro-2-methoxy-3-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]phenyl}ethyl)carbamate (190 mg, 0.39 mmol) in methanol (11 mL) was treated with 0.25 M HCl in water (3.9 mL, 0.98 mmol), degassed with nitrogen for 5 minutes, treated with 5% Pt/C (Degussa type) (96 mg, 50 wt %), and stirred under a balloon of hydrogen for 1 hour. The reaction mixture was filtered over a PTFE disposable filter. The filtrate was concentrated to give the desired product (180 mg, 99%) that was used without further purification. LCMS for C14H18Cl2F3N2O (M+H)+: m/z=357.1, 359.1. Found: 357.0, 359.0.

Workup

  1. customdegassed with nitrogen for 5 minutes
  2. additiontreated with 5% Pt/C (Degussa type) (96 mg, 50 wt %)
  3. filtrationThe reaction mixture was filtered over a PTFE disposable filter
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4794604e9ad14513b82514373499b0e1
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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