Sodium cyanoborohydride → HCID 178488390, compound

HRID 2174074Notes

Reaction equation

HRID 2174074 reaction equation
[CH3:1][O:2][C:3]([C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:19]=2[N:18]=1)([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)[CH3:4].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:19]=2[N:18]=1)([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH2:7][CH2:8][NH:9]2)[CH3:4]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 178489067HCID 178489067, compound

Product 1

HCID 178488390HCID 178488390, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-2-(1-Methoxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile (Example 27-B) (0.213 g, 0.591 mmol) was dissolved in acetic acid (1.970 mL), and sodium cyanoborohydride (0.12 g, 1.910 mmol) was added at room temperature. The reaction was stirred at the same temperature for 1 hour. The reaction was placed in an ice bath and quenched with 1N aq. NaOH (20 mL) until pH>7. EtOAc was added and the organic layer was removed, dried over MgSO4 and concentrated. The resulting residue was purified by flash chromatography (0-100% EtOAc in heptanes) to give the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.11 (s) 7.84 (m) 7.65 (s) 7.43-7.54 (m, 1H) 7.34-7.42 (m) 6.43 (s, 1H) 3.50-3.59 (m, 2H) 3.27-3.36 (m, 2H) 3.24 (s, 3H) 3.12 (s, 3H) 2.13 (s, 3H) 2.05 (s, 3H). HRMS calcd. for C21H22N4O2 (M+H)+, 303.1604. found 303.1615

Workup

  1. customThe reaction was placed in an ice bath
  2. customquenched with 1N aq. NaOH (20 mL) until pH>7
  3. additionEtOAc was added
  4. customthe organic layer was removed
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-db6fd940621e4961ac7ff4df30b7daf7
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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