Acetic Acid → HCID 9804267, compound

HRID 1635869Notes

Reaction equation

HRID 1635869 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([CH3:13])=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:14]([N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][N:19]2[CH:27]=[CH:28][CH:29]=[C:18]2[CH2:17]1)=[O:15].C(O)(=O)C.C=O>CO>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([CH3:13])=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:14]([N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][N:19]2[C:27]([CH2:14][N:16]([CH3:22])[CH3:17])=[CH:28][CH:29]=[C:18]2[CH2:17]1)=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5311500WAY-151932

Product 1

HCID 9804267HCID 9804267, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of [2-chloro-4-(3-methyl-pyrazol-1-yl)-phenyl]-(5H,11H-pyrrolo-[2,1-c][1,4]benzodiazepin-10-yl)-methanone (1.61 g), N, N, N′, N′, tetramethyldiamino-methane (0.82 g), and glacial acetic acid (0.48 g) in methanol (25 ml) was added a solution of 37% aqueous formaldehyde (4 ml). The mixture was warmed to 40° C. for 10 minutes. After stirring one hour at room temperature, the reaction was concentrated in vacuo, redissolved in dichloromethane, and extracted sequentially with aqueous sodium bicarbonate and water (4×). The organic phase was dried over anhydrous sodium sulfate, and filtered through a plug of silica gel, eluted with ethyl acetate. Evaporation of the solvent in vacuo afforded an oil, which on trituration with hexane yielded 0.36 g of the title compound as a colorless powder, m.p. 100-102° C.; MS (+FAB), m/z: 482 (M+Na)+, 460 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionredissolved in dichloromethane
  3. extractionextracted sequentially with aqueous sodium bicarbonate and water (4×)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered through a plug of silica gel
  6. washeluted with ethyl acetate
  7. customEvaporation of the solvent in vacuo
  8. customafforded an oil, which on trituration with hexane

Sources & evidence

ORD record
ord-0c99b9e8b5b4497da52897d7ad1a7035
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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