tert-Butoxy bis(dimethylamino)methane → HCID 18449080, compound

HRID 1270189Notes

Reaction equation

HRID 1270189 reaction equation
[CH:1]1([C:7]2[CH:31]=[CH:30][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](=[O:29])[CH3:28])=[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.C(O[CH:37](N(C)C)[N:38]([CH3:40])[CH3:39])(C)(C)C>ClCCl>[CH:1]1([C:7]2[CH:31]=[CH:30][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](=[O:29])/[CH:28]=[CH:37]/[N:38]([CH3:40])[CH3:39])=[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

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 10295173HCID 10295173, compound

Product 1

HCID 18449080HCID 18449080, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[10-(4-cyclohexylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]-ethanone of Example 6 Step B (1.0 g), tert-butoxybis(dimethylamino) methane (5 mL) and dichloromethane (25 mL) was refluxed for six hours and then allowed to stir at room temperature overnight. All volatiles were then removed at reduced pressure and the residue was dissolved in dichloromethane. The solution was washed with water, dried over anhydrous sodium sulfate and filtered through a short column of Magnesol®. The eluate was refluxed with the gradual addition of hexane to provide pale yellow crystals of the title compound (0.16 g), m.p. 237–240° C.

Workup

  1. temperaturewas refluxed for six hours
  2. customAll volatiles were then removed at reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of Magnesol®
  7. temperatureThe eluate was refluxed with the gradual addition of hexane

Sources & evidence

ORD record
ord-6d99a40db938444fa9c929e2fcf306fe
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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