Dimethylamine → HCID 15382237, compound

HRID 1007866Notes

Reaction equation

HRID 1007866 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-6d7ae6fbb32947c4959d1322d4a0adba
Source dataset
uspto-grants-2004_09
Patent number
US06797715B1

Reaction notes

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