Sodium cyanoborohydride → HCID 67416011, compound

HRID 912672Notes

Reaction equation

HRID 912672 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]2[CH:18]=O.Cl.Cl.[NH:22]1[C:26]([C:27]([NH2:29])=[O:28])=[CH:25][N:24]=[CH:23]1.C([BH3-])#[N:31].[Na+]>CO>[NH2:29][C:27]([C:26]1[NH:22][CH:23]=[N:24][C:25]=1[NH:31][CH2:18][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[N:7]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH:6]=1)=[O:28]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 217038501H-imidazole-5-carboxamide dihydrochlorideHCID 71466818HCID 71466818, compound

Product 1

HCID 67416011HCID 67416011, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 5-chloro-3-formyl-1H-indole-1-carboxylate (0.84 g, 3.0 mmol, obtained from Example 10(a)), 1H-imidazole-5-carboxamide dihydrochloride (0.49 g, 3.0 mmol) and sodium cyanoborohydride (0.45 g, 7.2 mmol) in MeOH (5 mL) was stirred at r.t for 19 h. The reaction mixture was partitioned between H2O (25 mL) and CHCl3 (3×25 mL), the combined organic phases were dried over MgSO4 and evaporated. Purification by flash chromatography on silica using a gradient of methanol (2-8%) in chloroform gave the title compound (0.30 g, 26%). MS (ESI) m/z 390 (M+1).

Workup

  1. customThe reaction mixture was partitioned between H2O (25 mL) and CHCl3 (3×25 mL)
  2. dry with materialthe combined organic phases were dried over MgSO4
  3. customevaporated
  4. customPurification by flash chromatography on silica using a gradient of methanol (2-8%) in chloroform

Sources & evidence

ORD record
ord-b87eaf2186984503838b44bc9547d8f3
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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