Acetic Acid → HCID 9955653, compound

HRID 2307389Notes

Reaction equation

HRID 2307389 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]2)[CH:6]=[CH:5][C:4]=1[C:15]([N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][N:20]2[CH:28]=[CH:29][CH:30]=[C:19]2[CH2:18]1)=[O:16].C(O)(=O)C.C=O>CO>[CH3:15][N:17]([CH2:23][C:28]1[N:20]2[C:19]([CH2:18][N:17]([C:15]([C:4]3[CH:5]=[CH:6][C:7]([N:9]4[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]4)=[CH:8][C:3]=3[O:2][CH3:1])=[O:16])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21]2)=[CH:30][CH:29]=1)[CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10200885HCID 10200885, compound

Product 1

HCID 9955653HCID 9955653, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of [2-methoxy-4-(3-methyl-pyrazol-1-yl)-phenyl](5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl) methanone from Example 107 (0.57 g) in warm methanol (10 ml) was added N,N,N,N′-tetramethyl-diaminomethane (0.392 ml) and acetic acid (0.164 ml). Following the addition of aqueous 37% formalin solution (2.9 ml) the reaction was stirred for fifteen minutes. The mixture was concentrated in vacuo and partitioned between dichloromethane and sodium hydrogen carbonate. The organic phase was removed, washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica eluting with chloroform/methanol (50/1) to afford a solid. Recrystallisation of the solid from acetone gave the title compound as a colorless solid, m.p. 196-198° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between dichloromethane and sodium hydrogen carbonate
  3. customThe organic phase was removed
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by flash column chromatography on silica eluting with chloroform/methanol (50/1)
  9. customto afford a solid
  10. customRecrystallisation of the solid from acetone

Sources & evidence

ORD record
ord-ae17bf9b730042a4b0c886719c114d86
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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