Sodium borohydride → (1H-Benzimidazol-2-ylmethyl)-(4-{[(1H-benzimidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 7175

Reaction equation

HRID 7175 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]=O.[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][N:30]([CH:40]1[C:49]2[N:48]=[CH:47][CH:46]=[CH:45][C:44]=2[CH2:43][CH2:42][CH2:41]1)[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH2:39])=[CH:34][CH:33]=1.[BH4-].[Na+]>CO>[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][N:30]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH:39][CH2:16][C:8]2[NH:7][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)=[CH:34][CH:33]=1)[CH:40]1[C:49]2[N:48]=[CH:47][CH:46]=[CH:45][C:44]=2[CH2:43][CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazoleHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 22018638(1H-Benzimidazol-2-ylmethyl)-(4-{[(1H-benzimidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amineYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 1-(2-trimethylsilylethoxymethyl)-2-formyl-benzimidazole (prepared as described by Bridger et al. U.S. patent application Ser. No. 09/535,314) (0.150 g, 0.54 mmol) in dry MeOH (2.5 mL) was added a dry MeOH (2.5 mL) solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.215 g, 0.54 mmol) under an argon atmosphere. The mixture was stirred at room temperature for 1.5 h then concentrated under reduced pressure and analyzed by 1H NMR. The residue was dissolved in dry MeOH (5 mL) and to the resultant solution was added sodium borohydride (41 mg, 1.08 mmol) and the reaction mixture stirred for 16 h (see General Procedures XX). Purification of the crude product by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 100:1:1 followed by 50:1:1) afforded the desired product (0.165 g, 47%) as a pale yellow oil.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dry MeOH (5 mL) and to the resultant solution
  3. stirringthe reaction mixture stirred for 16 h (see General Procedures XX)
  4. customPurification of the crude product by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 100:1:1 followed by 50:1:1)

Sources & evidence

ORD record
ord-0ff3ba42618041fc8e5a90fd6e987d41
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

Loading…