Dimethylformamide dimethyl acetal → HCID 22605454, compound

HRID 1635837Notes

Reaction equation

HRID 1635837 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>ClCCl>[CH3:28][N:29]([CH:31]=[N:23][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:16])=[CH:25][CH:24]=1)[CH3:30]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 9949425HCID 9949425, compound

Product 1

HCID 22605454HCID 22605454, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-benzamide (1.25 g) from Example 45 and dimethylformamide dimethylacetal (20 ml) was refluxed for 4 hours and the volatiles removed in vacuo to give a solid. The solid was dissolved in dichloromethane and filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a steam bath with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (1,40 g), m.p. 232-234° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customthe volatiles removed in vacuo
  3. customto give a solid
  4. filtrationfiltered through a short column of hydrous sodium magnesium silicate
  5. washfurther eluted with several volumes of dichloromethane
  6. concentrationThe combined organic phase was concentrated on a steam bath with the gradual addition of hexane until crystallization
  7. temperatureAfter cooling
  8. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-ab80f1fef1eb40c2993de093580c814a
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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