Acetic Acid → HCID 9884982, compound

HRID 2307346Notes

Reaction equation

HRID 2307346 reaction equation
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][N:18]3[CH:26]=[CH:27][CH2:28][C:17]3=[CH:16]2)=[O:14])=[CH:9][CH:8]=1)C.C(O)(=O)C.[NH2:34]N>ClCCl>[CH:28]1[CH:27]=[CH:26][N:18]2[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:15]([C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]4[NH:34][N:2]=[CH:4][N:5]=4)=[CH:8][CH:9]=3)=[O:14])[CH2:16][C:17]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 69919413HCID 69919413, compound

Product 1

HCID 9884982HCID 9884982, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(dimethylaminomethylene)-4-(5H,1 H-pyrrolo[2,1-c][1,4]-benzodiazepine-10-carbonyl)-benzamide (1.0 g) from Example 46, glacial acetic acid (15 ml), and anhydrous hydrazine (0.16 g) was refluxed for 15 hours and the volatiles removed in vacuo. Saturated aqueous sodium bicarbonate solution was added and the resultant solid was recovered by filtration. The solid 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 (0.39 g), m.p. 225-227° C.; MS, m/z: 355 (M)+.

Workup

  1. temperaturewas refluxed for 15 hours
  2. customthe volatiles removed in vacuo
  3. additionSaturated aqueous sodium bicarbonate solution was added
  4. filtrationthe resultant solid was recovered by filtration
  5. temperatureThe solid was refluxed for 4 hours
  6. customthe volatiles removed in vacuo
  7. customto give a solid
  8. filtrationfiltered through a short column of hydrous sodium magnesium silicate
  9. washfurther eluted with several volumes of dichloromethane
  10. concentrationThe combined organic phase was concentrated on a steam bath with the gradual addition of hexane until crystallization
  11. temperatureAfter cooling
  12. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-7b9494be55934618a17b30e7a2c1ac2e
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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