1-Hydroxybenzotriazole → HCID 67783239, compound

HRID 1647821Notes

Reaction equation

HRID 1647821 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]1=[O:19].ON1C2C=CC=CC=2N=N1.[C:30]([C:33]1[N:34]=[CH:35][C:36]2[NH:37][C:38]3[C:43]([C:44]=2[CH:45]=1)=[CH:42][CH:41]=[CH:40][CH:39]=3)(O)=[O:31].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(N(CC)CC)C>[CH:35]1[C:36]2[NH:37][C:38]3[C:43]([C:44]=2[CH:45]=[C:33]([C:30]([C:2]2([NH2:1])[CH2:8][CH2:7][C:6]4[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=4[N:4]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:3]2=[O:19])=[O:31])[N:34]=1)=[CH:42][CH:41]=[CH:40][CH:39]=3

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19921039HCID 19921039, compound

Product 1

HCID 67783239HCID 67783239, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

In 15 ml of dimethylformamide were dissolved 0.252 g of 3-amino-1-phenyl-2,3,4,5-tetrahydro-1-benzoazepin-2(1H)-one, 0.127 g of 1-hydroxybenzotriazole, 0.223 g of 3-carboxy-β-carboline and 0.2 g of 1-ethyl-3-(3'-dimethylaminopropyl)-carbodiimide hydrochloride and 0.5 ml of triethylamine was added to the solution, and the mixture was stirred at room temperature for one day. After the solvent was removed under reduced pressure, a 10% aqueous citric acid and chloroform were added to the residue and the mixture was stirred. Thereafter, the chloroform layer was separated, washed with a 10% sodium hydroxide aqueous solution and then with water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and ethyl acetate was added to the residue. The precipitates were collected by filtration to obtain 0.312 g of the title compound as crystals. Melting point: 302° to 304° C., IR (Nujol) (cm-1): 3360, 3290, 1730, 1670, 1650, 1625, MS (m/z): 446 (M+), 264 (base)

Workup

  1. additionwas added to the solution
  2. customAfter the solvent was removed under reduced pressure
  3. additiona 10% aqueous citric acid and chloroform were added to the residue
  4. stirringthe mixture was stirred
  5. customThereafter, the chloroform layer was separated
  6. washwashed with a 10% sodium hydroxide aqueous solution
  7. dry with materialwith water, and dried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure, and ethyl acetate
  9. additionwas added to the residue
  10. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-b3bf96cb532741c09ff00ec295eae028
Source dataset
uspto-grants-1995_07
Patent number
US05434148

Reaction notes

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