Dimethylamine → HCID 15382237, compound

HRID 720496Notes

Reaction equation

HRID 720496 reaction equation
[CH2:1]([C:3]1([OH:28])[C:25]2[CH:24]=[C:23]3[N:10]([CH2:11][C:12]4[C:13]3=[N:14][C:15]3[CH:16]=[CH:17][C:18]([OH:22])=[CH:19][C:20]=3[CH:21]=4)[C:9](=[O:26])[C:8]=2[CH2:7][O:6][C:5](=[O:27])[CH2:4]1)[CH3:2].[CH2:29]=O.[CH3:31][NH:32][CH3:33]>C(O)(=O)C>[CH3:31][N:32]([CH2:29][C:19]1[C:20]2[CH:21]=[C:12]3[CH2:11][N:10]4[C:23](=[CH:24][C:25]5[C:3]([CH2:1][CH3:2])([OH:28])[CH2:4][C:5](=[O:27])[O:6][CH2:7][C:8]=5[C:9]4=[O:26])[C:13]3=[N:14][C:15]=2[CH:16]=[CH:17][C:18]=1[OH:22])[CH3:33]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 11143351HCID 11143351, compound

Product 1

HCID 15382237HCID 15382237, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 5-ethyl-5,10-dihydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3′,4′:6,7]indolizino[1,2-b]quinoline-3,15-dione (260 mg, 0,69 mmol) in acetic acid (15 ml) is treated with aqueous formaldehyde at 37% (500 μl) and aqueous dimethylamine at 40% (500 μl) and the resultant mixture is agitated at ambient temperature for 16 hours. The reaction mixture is concentrated to dryness and the residue is purified by column chromatography (SiO2, CH2Cl2/MeOH: 100/0 to 90/10) followed by crystallization from acetonitrile, which produces 102 mg of sought compound.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customthe residue is purified by column chromatography (SiO2, CH2Cl2/MeOH: 100/0 to 90/10)
  3. customfollowed by crystallization from acetonitrile, which

Sources & evidence

ORD record
ord-fb07d06e33174e9db586393b1d8d1391
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

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