Hydrochloric Acid → HCID 58424880, compound

HRID 2409432Notes

Reaction equation

HRID 2409432 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:13]2[CH:14]=[CH:15][C:16]([CH2:18][CH2:19][CH:20]=O)=[CH:17][C:12]=2[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]1=[O:22].[CH3:23][NH:24][CH3:25].C([BH3-])#N.[Na+].Cl>CO>[CH3:23][N:24]([CH3:25])[CH2:20][CH2:19][CH2:18][C:16]1[CH:15]=[CH:14][C:13]2[N:4]([CH2:3][O:2][CH3:1])[C:5](=[O:22])[C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[C:12]=2[CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 58424889HCID 58424889, compound

Product 1

HCID 58424880HCID 58424880, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (151 mg, 0.51 mmol) prepared in step 7 was dissolved in methanol, sequentially added with 2 M dimethylamine (2.18 ml, 4.38 mmol), sodium cyanoborohydride (35 mg, 0.56 mmol), zinc chloride(II) (35 mg, 0.255 mmol), and 1.25 M hydrochloric acid (2.44 ml, 3.06 mmol) at 0° C. The resulting mixture was stirred for one hour at room temperature. The mixture was poured into ice water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was then purified by flash column chromatography (chloroform:methanol=15:1) to obtain the title compound (152 mg, yield: 92%, white solid).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue was then purified by flash column chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-99db3cf5b81945778615aa042853b394
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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