Sodium Hydroxide → HCID 178442276, compound

HRID 2174138Notes

Reaction equation

HRID 2174138 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:13]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][C:25]([C:27]#[N:28])=[CH:26][C:20]=3[N:19]=2)([CH2:15][CH:16]=[CH2:17])[CH3:14])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([C:13]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][C:25]([C:27]#[N:28])=[CH:26][C:20]=3[N:19]=2)([CH2:15][CH:16]=[CH2:17])[CH3:14])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 178442277HCID 178442277, compound

Product 1

HCID 178442276HCID 178442276, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-2-(2-(5-methoxy-7-methyl-1H-indol-4-yl)pent-4-en-2-yl)-1H-benzo[d]imidazole-5-carbonitrile (Example 156-F) (150 mg, 0.405 mmol) in acetic acid (2.025 mL) was added sodium cyanoborohydride (38.2 mg, 0.607 mmol) and the reaction was stirred at room temperature for 1 hour. At this point the mixture was placed in an ice bath and quenched with NaOH (17.61 mL, 35.2 mmol) and then diluted with DCM. The layers were separated and the organic layer was dried over sodium sulfate, concentrated and absorbed onto silica and purified via FCC (0-100% EtOAc:heptanes) to give the title compound. MS (ESI+) m/z 373.3 (M+H).

Workup

  1. customAt this point the mixture was placed in an ice bath
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customabsorbed onto silica
  6. custompurified via FCC (0-100% EtOAc:heptanes)

Sources & evidence

ORD record
ord-75fcea73c4ea4042824137356907976d
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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