Benzyl carbazate → HCID 68470517, compound

HRID 507377Notes

Reaction equation

HRID 507377 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.[CH2:17]([O:24][C:25]([NH:27][NH2:28])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH2:17]([O:24][C:25]([NH:27][N:28]=[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:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 79242Benzyl carbazateHCID 99908943-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde

Product 1

HCID 68470517HCID 68470517, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 50 ml flask is charged with 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde (Reference Example 9; 2.16 g, 10 mmol), hydrazinecarboxylic acid benzyl ester (1.66 g, 10 mmol), and methanol (30 ml). This mixture is heated at reflux over night, and then the solvent is removed on the rotavapor to leave the hydrazone as a foam. 1H-NMR (CDCl3, 300 MHz) δ 2.24 (s, 6H, N(CH3)2); 2.55, 2.81 (2 m, 2H each, CH2CH2NHMe2); 5.22 (s, 2H, OCH2); 6.86 (d, 1H, J=2 Hz, H-2); 7.09 (d, 1H, J=8.5 Hz, H-7); 7.23-7.36 (m, Ph-H); 7.43 (dd, 1H, J=1.5 Hz, H-6); 7.62 (d, 1H, H-4); 7.79 (br s, 1H, N═CH); 9.35 (br s, NH); 9.50 (s, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 23.57 (CH2); 45.36 (N(CH3)2); 60.26 (CH2NMe2); 67.47 (OCH2); 112.17 (C-7); 114.3 (C-3); 119.51 (C-4); 120.69 (C-6); 123.32 (C-2); 125.15 (C-5); 127.48 (C-9); 128.33, 128.50 (2C), 128.73 (2C), 136.40 (q) (Ph C); 137.76 (C-8) 147.50 (N═CH); 154.10 (NC═O).

Workup

  1. temperatureThis mixture is heated
  2. temperatureat reflux over night
  3. customthe solvent is removed on the rotavapor

Sources & evidence

ORD record
ord-0fb27cc4eee148eeb86aa21ede6d9ce5
Source dataset
uspto-grants-2010_08
Patent number
US07786156B2

Reaction notes

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