Methanol → HCID 86679688, compound

HRID 1041917Notes

Reaction equation

HRID 1041917 reaction equation
CO.[NH2:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[N:6]([C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:26][CH:25]=1)[C:7](=[O:23])[N:8]2[C@@H:13]1[CH2:17][CH2:16][N:15]([C:18](=[O:22])[C:19]#[C:20][CH3:21])[CH2:14]1.[BH4-].[Na+]>C(OCC)(=O)C>[NH2:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[N:6]([C:24]1[CH:29]=[CH:28][C:27]([CH:30]([OH:37])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:26][CH:25]=1)[C:7](=[O:23])[N:8]2[C@@H:13]1[CH2:17][CH2:16][N:15]([C:18](=[O:22])[C:19]#[C:20][CH3:21])[CH2:14]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86679689HCID 86679689, compound

Product 1

HCID 86679688HCID 86679688, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A methanol (1 mL) solution of the compound (30 mg) prepared in Example 19(40) was cooled to 0° C.; sodium borohydride (2.4 mg) was added; and stirring was carried out for 30 minutes. The reaction mixture was diluted with ethyl acetate and was then washed with water and a saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate followed by concentration under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=10:1) to obtain the title compound (28 mg) having the physical property values indicated below.

Workup

  1. washwas then washed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationfollowed by concentration under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-0539e6b01e9a47adbea310d90e2a2129
Source dataset
uspto-grants-2013_10
Patent number
US08557803B2

Reaction notes

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