Water → HCID 18318491, compound

HRID 1700777Notes

Reaction equation

HRID 1700777 reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].C[Al](C)C.C([O:11][C:12](=O)[CH2:13][O:14][C:15]1[CH:44]=[CH:43][C:18]([CH2:19][C:20]2[C:21]3[CH:42]=[CH:41][CH:40]=[CH:39][C:22]=3[S:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=2)=[CH:17][CH:16]=1)C.O>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:4])[NH:3][C:12](=[O:11])[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][C:20]2[C:21]3[CH:42]=[CH:41][CH:40]=[CH:39][C:22]=3[S:23][C:24]=2[C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)=[CH:29][CH:30]=2)=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 962WaterHCID 59761,1-DimethylhydrazineHCID 16682925TrimethylaluminumHCID 18318442HCID 18318442, compound

Product 1

HCID 18318491HCID 18318491, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 1,1-dimethyl hydrazine (0.1 mL, 1.3 mmol) in toluene (5 mL) was added to a solution of trimethyl aluminum (1.3 mL, 1.0M/toluene) in toluene (20 mL) at 0-5° C. The cooling bath was removed and the mixture stirred for 60 minutes. A solution of 3-[4-(2-ethoxy-2-oxoethoxy)benzyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-benzo[b]thiophene (310 mg, 0.6 mmol) in toluene (5-10 mL) was added and the mixture refluxed for 60 minutes, cooled, decomposed with water, and extracted with CH2Cl2:i-PrOH (3:1). The organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient (CH2Cl2/5% MeOH/0-1% Et3N) to give the title compound as an amorphous solid (205 mg, 65%).

Workup

  1. customThe cooling bath was removed
  2. temperaturethe mixture refluxed for 60 minutes
  3. temperaturecooled
  4. extractionextracted with CH2Cl2:i-PrOH (3:1)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel
  9. washeluting with a gradient (CH2Cl2/5% MeOH/0-1% Et3N)

Sources & evidence

ORD record
ord-60f07bcdca8b499c9a73c9c5c5e527b1
Source dataset
uspto-grants-2002_02
Patent number
US06350774B1

Reaction notes

Loading…