Dimethylamine → HCID 67874066, compound

HRID 1418705Notes

Reaction equation

HRID 1418705 reaction equation
I[CH2:2][C:3]([O:5][CH2:6][C:7]1[C:8](=[O:28])[N:9]2[C:21](=[CH:22][C:23]=1[C:24](=[O:27])[CH2:25][CH3:26])[C:12]1=[N:13][C:14]3[C:19]([CH:20]=[C:11]1[CH2:10]2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:4].[NH:29]([CH3:31])[CH3:30].C(Cl)[Cl:33]>>[ClH:33].[CH3:30][N:29]([CH2:2][C:3]([O:5][CH2:6][C:7]1[C:8](=[O:28])[N:9]2[C:21](=[CH:22][C:23]=1[C:24](=[O:27])[CH2:25][CH3:26])[C:12]1=[N:13][C:14]3[C:19]([CH:20]=[C:11]1[CH2:10]2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:4])[CH3:31]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 6344Dichloromethane2×HCID 54564324HCID 54564324, compound

Product 1

HCID 67874066HCID 67874066, compound

Procedure

A suspension of 8-[[(iodoacetyl)oxy]methyl]-7-(1-oxopropyl)indolizino[1,2-b]quinolin-9(11H)-one (48.8 mg, 0.098 mmol) in dry CH2Cl2 (5.0 mL) was covered by an atmosphere of (CH3)2NH (balloon). Within a few min the solid had dissolved and after 5 min the reaction was stripped to dryness. The residue was dissolved in CH2Cl2, washed first with 5% aqueous NaHCO3 and then with H2O, and dried over Na2SO4. The solvent was removed in vacuo, and the residue was suspended in H2O (20 mL) to which was added 1N HCl (100 μL) to dissolve most of the solid. After filtration, lyophilization gave the title compound. 1H NMR (CDCl3 /MeOH-d4) d 8.47 (s, 1H), 8.23 (d, J=8.3 Hz, 1H), 7.98 (d, J=7.5 Hz, 1H), 7.87 (m, 1H), 7.71 (m, 1H), 7.44 (s, 1H), 5.38 (s, 2H), 5.35 (s, 2H), 3.95 (s, 2H), 3.05 (s, 6H), 3.02 (q, J=7.1 Hz, 2H), 1.27 (t, J=7.1 Hz, 3H). Anal. Calcd for C23H23N3O4.HCl.7/4 H2O: C, 58.35; H, 5.86; N, 8.88. Found: C, 58.26; H, 5.51; N, 8.68.

Workup

  1. dissolutionWithin a few min the solid had dissolved and after 5 min the reaction
  2. washwashed first with 5% aqueous NaHCO3
  3. dry with materialwith H2O, and dried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. additionwas added 1N HCl (100 μL)
  6. dissolutionto dissolve most of the solid
  7. filtrationAfter filtration, lyophilization

Sources & evidence

ORD record
ord-154ebb54a6ea410bbb85ed5b7ad167eb
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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