Trimethyl orthoformate → N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzylidene)-N',N'-dipropyl-butane-1,4-diamine

HRID 2080896Notes

Reaction equation

HRID 2080896 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[CH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[CH2:24]([N:27]([CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])[CH2:25][CH3:26].C(OC)(OC)OC>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[N:32][CH2:31][CH2:30][CH2:29][CH2:28][N:27]([CH2:33][CH2:34][CH3:35])[CH2:24][CH2:25][CH3:26])=[CH:18][CH:17]=1)[CH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 7138396N,N-dipropylbutane-1,4-diamineHCID 866149184-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzaldehyde

Product 1

HCID 67103803N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzylidene)-N',N'-dipropyl-butane-1,4-diamineYield 103.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (210 mg) obtained in Example 84-5 was dissolved in anhydrous methanol (6.3 ml) and added with the compound (117 mg) obtained in Example 1-2. The solution was added with trimethyl orthoformate (297 μl) and the whole was stirred at room temperature for 6.5 hours. After completion of the reaction, the solvent was distilled off, thereby obtaining the subject compound (325 mg) as a brown oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-e7731e41b0d8455ba2f8e92f61c3a335
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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