Hydrochloric Acid → HCID 68546719, compound

HRID 2241922Notes

Reaction equation

HRID 2241922 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:30]COCCOC)=[C:8]([CH:29]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25](=[O:27])[CH3:26])[CH2:20][CH2:19]2)=[C:14]([F:28])[CH:13]=1)=[O:10].Cl>CO>[ClH:3].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([OH:30])=[C:8]([CH:29]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH:25]([OH:27])[CH3:26])[CH2:22][CH2:23]2)=[C:14]([F:28])[CH:13]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59205012HCID 59205012, compound

Product 1

HCID 68546719HCID 68546719, compoundYield 187%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.038 g, 1.00 mmol) was added to a solution of 5-chloro-N-{3-fluoro-4-[4-(2-oxopropan-1-yl)piperazin-1-yl]phenyl}-2-(2-methoxyethoxy methoxy)benzamide (compound of Reference Example 144; 0.134 g, 0.272 mmol) in methanol (1 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour. 0.5N Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated under reduced pressure. The precipitated solid was collected by filtration and washed with water. 2N Hydrochloric acid was added to the obtained solid, and the mixture was refluxed for 1 hour. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration and washed with acetone to give the title compound (0.113 g, 93%) as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. addition2N Hydrochloric acid was added to the obtained solid
  5. temperaturethe mixture was refluxed for 1 hour
  6. temperatureThe reaction mixture was cooled to room temperature
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed with acetone

Sources & evidence

ORD record
ord-9a1834fe48804cff99fcfc969c339dff
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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