Succinic anhydride → HCID 11293419, compound

HRID 1668841Notes

Reaction equation

HRID 1668841 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([NH:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[C:24]2[C:19](=[C:20]([CH3:32])[C:21]3[NH:27][C:26]4[CH:28]=[CH:29][N:30]=[CH:31][C:25]=4[C:22]=3[CH:23]=2)[CH:18]=[CH:17][N:16]=1)[CH3:9]>C1(C)C=CC=CC=1>[CH2:8]([N:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15]1[C:24]2[C:19](=[C:20]([CH3:32])[C:21]3[NH:27][C:26]4[CH:28]=[CH:29][N:30]=[CH:31][C:25]=4[C:22]=3[CH:23]=2)[CH:18]=[CH:17][N:16]=1)[C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH3:9]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 30688641,3-Propanediamine, N-ethyl-N'-(6-methyl-5H-pyrido(3',4':4,5)pyrrolo(2,3-g)isoquinolin-10-yl)-, hemihydrate

Product 1

HCID 11293419HCID 11293419, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 75 mg of succinic anhydride (0.75 mM) and 250 mg (0.75 mM) of N-ethyl-N′-(6-methyl-5H-pyrido[3′,4′:4,5]pyrrolo[2,3-g]isoquinolin-10-yl)propane-1,3-diamine in 80 ml of dry toluene was brought to reflux for 4 h. The precipitate obtained after cooling was dried and recrystallized with acetone. 240 mg (65.6%) was obtained in the form of solid (F˜150°). Centesimal analysis for C24H27N5O3+3H2O; Calc.: C, 59.12; H, 6.82; N, 14.37; Exp.; C, 59.14; H, 6.88; N, 14.17. NMR and MS in agreement.

Workup

  1. temperatureto reflux for 4 h
  2. customThe precipitate obtained
  3. temperatureafter cooling
  4. customwas dried
  5. customrecrystallized with acetone
  6. custom240 mg (65.6%) was obtained in the form of solid (F˜150°)

Sources & evidence

ORD record
ord-2f78a266da7641dd968034cfdb4b43bf
Source dataset
uspto-grants-2011_08
Patent number
US07989467B2

Reaction notes

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