Sodium → HCID 12001495, compound

HRID 503216Notes

Reaction equation

HRID 503216 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25](=[O:27])[CH3:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:14][CH:15]=2)=[N:5][CH:4]=[N:3]1.[Na]>CN(C=O)C.CO>[CH3:1][N:2]1[C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([CH:25]([OH:27])[CH3:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:14][CH:15]=2)=[N:5][CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 12001407HCID 12001407, compound

Product 1

HCID 12001495HCID 12001495, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 21d (4.9 g, 13.9 mmol) in a mixture of DMF (90 ml) and methanol (10 ml) was added sodium boronhydride (0.53 g, 13.9 mmol). The resultant mixture was stirred at 60° C. for 1 hour. The cooled mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulphate and eluted through silica gel with a mixture of ethyl acetate and methanol (9:1 v/v). The pure fractions were concentrated and compound 23 was precipitated as the hydro chloride upon addition of etheral hydrogen chloride to the concentrate. Yield: 46%. LC-ESI-HRMS of [M+H]+ shows 364.1764 Da. Calc. 364.177325 Da, dev. −2.5 ppm

Workup

  1. customThe cooled mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. washeluted through silica gel with a mixture of ethyl acetate and methanol (9:1 v/v)
  5. concentrationThe pure fractions were concentrated
  6. customcompound 23 was precipitated as the hydro chloride upon addition of etheral hydrogen chloride to the concentrate

Sources & evidence

ORD record
ord-3a0a627c5dd142fca3bbb683b1dc11a8
Source dataset
uspto-grants-2010_08
Patent number
US07776900B2

Reaction notes

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