Pyridine → HCID 87540558, compound

HRID 2244253Notes

Reaction equation

HRID 2244253 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)=O.Cl.[NH2:42][OH:43].N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:43]/[N:42]=[CH:1]/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 15952274HCID 15952274, compound

Product 1

HCID 87540558HCID 87540558, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10-[(2′-formyl-1,1′-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 56 (0.500 g, 0.95 mmol) and hydroxylamine hydrochloride (0.132 g, 1.90 mmol) in methanol (15 mL) was added pyridine (0.155 mL, 1.90 mmol) and the reaction mixture heated to reflux under nitrogen for 1 hour. The cooled reaction mixture was then poured into 5% w/v aqueous sodium carbonate solution (100 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a white foam. Crystallization of the crude product from dichloromethane gave the title compound (0.458 g, 89%) as a white crystalline solid, m.p. 165-167° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux under nitrogen for 1 hour
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (100 mL)
  5. extractionThe organic extract
  6. washwas washed with water (100 mL) and brine (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto afford a white foam
  10. customCrystallization of the crude product from dichloromethane

Sources & evidence

ORD record
ord-27fabff6c6b44187971113dd4c3ffc29
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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