Acetic Acid → [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amine

HRID 2080742Notes

Reaction equation

HRID 2080742 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:15]2)=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].[CH3:33][N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[CH:39]=O.C(O)(=O)C>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:15]2)=[CH:11][CH:10]=1)[CH2:39][C:35]1[N:34]([CH3:33])[CH:38]=[CH:37][N:36]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23155525[4-(6-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amine

Product 1

HCID 58345790[4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amineYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (27.3 mg) obtained in Example 11-14 was dissolved in methanol (1.37 ml) and added with sodium cyanoborohydride (9.0 mg) and 1-methyl-2-imidazole carboxaldehyde (11.8 mg). The solution was adjusted to pH 4 by addition of acetic acid, followed by stirring at room temperature for 3 hours. Then, the reaction solution was concentrated under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (31.5 mg) of the subject compound as a white solid.

Workup

  1. concentrationThen, the reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  7. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-90a0bb3029724c10b770ff7dd730806f
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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