1,1-Dimethoxyethyl(dimethyl)amine → HCID 69510551, compound

HRID 1270186Notes

Reaction equation

HRID 1270186 reaction equation
[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:24]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO[C:35](OC)([N:37]([CH3:39])[CH3:38])[CH3:36]>>[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:24]([C:27]([NH:29][N:30]=[C:35]([N:37]([CH3:39])[CH3:38])[CH3:36])=[O:28])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 10113410HCID 10113410, compound

Product 1

HCID 69510551HCID 69510551, compound

Procedure

A stirred mixture of 10-(4-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid hydrazide of Example 8 (0.50 g) and N,N-dimethylacetamide dimethyl acetal (5 mL) was refluxed for one hour and then evaporated to dryness under reduced pressure. The residue was dissolved in dichloromethane, washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and filtered through a short column of Magnesol®. After eluting with several additional volumes of dichloromethane, the combined eluate was evaporated to provide the title compound as a light tan amorphous solid, m.p. 164–175° C.

Workup

  1. temperaturewas refluxed for one hour
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of Magnesol®
  7. washAfter eluting with several additional volumes of dichloromethane
  8. customthe combined eluate was evaporated

Sources & evidence

ORD record
ord-3f1c55df122447029efb36ffb1fd06b8
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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