tert-Butyl carbazate → HCID 68472205, compound

HRID 507376Notes

Reaction equation

HRID 507376 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[NH:7][CH:6]=1.[C:17]([O:21][C:22]([NH:24][NH2:25])=[O:23])([CH3:20])([CH3:19])[CH3:18]>CO>[C:17]([O:21][C:22]([NH:24][N:25]=[CH:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:4][CH2:3][N:2]([CH3:16])[CH3:1])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 99908943-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde

Product 1

HCID 68472205HCID 68472205, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 ml flask is charged with 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde (Reference Example 9; 2.16 g, 10 mmol), hydrazinecarboxylic acid tert-butyl ester (1.32 g, 10 mmol), and methanol (10 ml). This mixture is heated at reflux for 18 hours, and then the solvent is removed on the rotavapor to leave the hydrazone (3.24 g, 98%). 1H-NMR (CDCl3, 300 MHz) δ 1.55 (s, 9H, C(CH3)3); 2.30 (s, 6H, N(CH3)2); 2.59, 2.87 (2 m, 2H each, CH2CH2NHMe2); 6.94 (d, 1H, J=2 Hz, H-2); 7.17 (d, 1H, J=8.5 Hz, H-7); 7.52 (dd, 1H, J=1.5 Hz, H-6); 7.68 (d, 1H, H-4); 7.84 (br s, 1H, N═CH); 8.42 (br s, NH); 9.10 (s, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 23.89 (CH2); 28.83 (C(CH3)3); 45.66 (N(CH3)2); 60.47 (CH2NMe2); 81.23 (OCMe3); 111.94 (C-7); 114.77 (C-3); 119.30 (C-4); 120.76 (C-6); 122.91 (C-2); 125.37 (C-5); 127.48 (C-9); 137.54 (C-8); 146.13 (N═CH); 153.13 (NC═O).

Workup

  1. temperatureThis mixture is heated
  2. temperatureat reflux for 18 hours
  3. customthe solvent is removed on the rotavapor

Sources & evidence

ORD record
ord-05333fdbad67462fa75d4e92843698c4
Source dataset
uspto-grants-2010_08
Patent number
US07786156B2

Reaction notes

Loading…