Acetaldehyde → HCID 86664530, compound

HRID 1910725Notes

Reaction equation

HRID 1910725 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O:22][C:23]([N:25]1[C:29]2[CH:30]=[C:31]([NH2:34])[CH:32]=[CH:33][C:28]=2[N:27]=[CH:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].[NH:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[N:36]1.[CH:44](=O)[CH3:45]>C1(C)C=CC=CC=1.CCCCCCC>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][CH:18]([N:35]3[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=4[N:37]=[N:36]3)[CH3:19])=[CH:16][C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:18]([O:22][C:23]([N:25]1[C:29]2[CH:30]=[C:31]([NH:34][CH:44]([N:35]3[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=4[N:37]=[N:36]3)[CH3:45])[CH:32]=[CH:33][C:28]=2[N:27]=[CH:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 219070151,1-Dimethylethyl 6-amino-1H-benzimidazole-1-carboxylateHCID 53406968tert-Butyl 5-amino-1H-benzo[d]imidazole-1-carboxylateHCID 178418385HCID 178418385, compound

Product 2

HCID 86664530HCID 86664530, compoundHCID 86664531HCID 86664531, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8900HeptaneSolvent

Procedure

[Step 1] 3.2 g of a mixture of tert-butyl-5-amino-1H-benzo[d]imidazole-1-carboxylate and tert-butyl-6-amino-1H-benzo[d]imidazole-1-carboxylate and 671 mg of 1H-benzotriazole was dissolved in 90 mL of toluene followed by adding 6 mL of a toluene solution containing 0.9 mL of acetoaldehyde and stirring overnight at room temperature. Following completion of the reaction, 30 mL of heptane were added followed by stirring for 1 hour and concentrating under reduced pressure to obtain 5.2 g of a crude produce of tert-butyl-5-[1-(1H-benzo[d][1,2,3]triazol-1-yl)ethylamino]-1H-benzo[d]imidazole-1-carboxylate and tert-butyl-6-[1-(1H-benzo[d][1,2,3]triazol-1-yl)ethylamino]-1H-benzo[d]imidazole-1-carboxylate.

Workup

  1. additionwere added
  2. stirringby stirring for 1 hour
  3. concentrationconcentrating under reduced pressure
  4. customto obtain 5.2 g of a crude

Sources & evidence

ORD record
ord-76573f759cf5461ea387da036800e2d5
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

Loading…