Sodium Acetate → HCID 54527618, compound

HRID 1601078Notes

Reaction equation

HRID 1601078 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[NH:12][CH:11]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10](=[O:18])[N:9]([CH3:19])[CH2:8][C:7]=2[CH:20]=1)=O.C([O-])(=O)C.[Na+].Cl.Cl.[NH2:28][CH2:29][C:30]1[NH:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1.C([BH3-])#N.[Na+]>CO>[N:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[NH:34][C:30]=1[CH2:29][NH:28][CH2:1][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][CH:11]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10](=[O:18])[N:9]([CH3:19])[CH2:8][C:7]=2[CH:20]=1

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 2723957(1H-benzo[d]imidazol-2-yl)methanamine dihydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 53691861HCID 53691861, compound

Product 1

HCID 54527618HCID 54527618, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (±)-7-formyl-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (180 mg, 0.65 mmol) (prepared as in Example 14(b)) was suspended in anhydrous methanol, then sodium acetate (160 mg, 1.95 mmol), 2-(amino methyl)benzimidazole dihydrochloride (143 mg, 0.65 mmol) and 4 Å molecular sieves were added. After 30 min., sodium cyanoborohydride (45 mg, 0.71 mmol) was added in 2 portions over a period of 30 min. The reaction mixture was allowed to stir at RT overnight, then the methanol was removed under vacuum. The residue was diluted with CH2Cl2, and the solution was washed with saturated NaHCO3. Drying (MgSO4), concentration, and silica gel chromatography (90% CH2Cl2 /9% methanol/1% NEt3) gave the title compound (133 mg, 49%): 1H NMR (CDCl3, 400 MHz) δ 2.67 (dd, J=16.1, 6.1 Hz, 1H), 2.96 (dd, J=16.1, 6.8 Hz, 1H), 3.05 (s, 3H), 3.68 (d, J=16.4 Hz), 3.72 (br s, 2H), 3.75 (s, 3H), 4.11 (br s, 2H, 4.97 (dd, J=6.8 Hz, 6.1, 1H), 5.35 (d, J=16.4 Hz, 1H), 6.54 (d, J=8.1 Hz, 1H), 6.87 (s, 1H), 7.05 (d, J=8.2 Hz, 1H), 7.20-7.26 (m, 2H), 7.57 (m, 2H); MS(ES) m/e 408 (M+H)+.

Workup

  1. customthe methanol was removed under vacuum
  2. additionThe residue was diluted with CH2Cl2
  3. washthe solution was washed with saturated NaHCO3
  4. customDrying
  5. concentration(MgSO4), concentration, and silica gel chromatography (90% CH2Cl2 /9% methanol/1% NEt3)

Sources & evidence

ORD record
ord-3b12fa0ba68a4b18b22cabfb841447be
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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