Dimethylformamide → HCID 91074791, compound

HRID 1519479Notes

Reaction equation

HRID 1519479 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13](=[O:31])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][C:15]=2[CH3:30])[C:8]2[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:7]1=2)=[O:4].Cl.[NH:38]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH3:39].[C:46](=[O:49])([O-:48])[O-].[K+].[K+].CN(C)C=O>O>[CH2:44]([O:43][C:41]([CH2:40][N:38]([CH3:39])[C:46]([O:48][CH2:2][C:3]([O:5][CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13](=[O:31])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][C:15]=2[CH3:30])[C:8]2[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:7]1=2)=[O:4])=[O:49])=[O:42])[CH3:45]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 25134204HCID 25134204, compound

Product 1

HCID 91074791HCID 91074791, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

{7-Chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} chloroacetate (500 mg, 0.95 mmol), ethyl sarcosinate hydrochloride (230 mg, 1.5 mmol), and potassium carbonate (414 mg, 3.0 mmol) were added to dimethylformamide (DMF) (5 ml), and the mixture was stirred at 60° C. for 1 hour. Water was added to the reaction mixture, and the resulted precipitates were collected by filtration and washed with water. The precipitates were dissolved in ethyl acetate, dried over anhydrous sodium sulfate, filtrated and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (n-hexane:ethyl acetate=36:64→15:85). The purified product was concentrated under reduced pressure. Water was added the residue, and resulted precipitates were collected by filtration and dried to obtain 330 mg of {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} (ethoxycarbonylmethyl-methyl-carbamoyloxy)acetate as white powder.

Workup

  1. customthe resulted precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. dissolutionThe precipitates were dissolved in ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash chromatography (n-hexane:ethyl acetate=36:64→15:85)
  9. concentrationThe purified product was concentrated under reduced pressure
  10. additionWater was added the residue
  11. customresulted
  12. customprecipitates
  13. filtrationwere collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-66b0dc063d0c42e8b917e5f50fd6a6f9
Source dataset
uspto-grants-2015_07
Patent number
US09073868B2

Reaction notes

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