Hydrochloric Acid → HCID 135725112, compound

HRID 1369934Notes

Reaction equation

HRID 1369934 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[O:17][CH:18]=[C:19]([CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=O)[CH3:31])=[CH:26][CH:25]=3)[N:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[CH3:37][NH:38][CH3:39].[ClH:40]>C(Cl)Cl>[ClH:40].[C:12]([C:9]1[CH:8]=[C:7]([C:16]2[O:17][CH:18]=[C:19]([CH2:21][CH2:22][O:23][C:24]3[CH:25]=[CH:26][C:27]([CH:30]([N:38]([CH3:39])[CH3:37])[CH3:31])=[CH:28][CH:29]=3)[N:20]=2)[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:10]=1[OH:11])([CH3:13])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 135725069HCID 135725069, compound

Product 1

HCID 135725112HCID 135725112, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Title compound was prepared substantially in accordance with the procedure in Example 1E above using the compound of Step A, 1.23 g (19.5 mmole) of sodium cyanoborohydride and dimethylamine (19.4 ml, 293 mmole), heating to 60° C. for 24 hours. The organic layer was chromatographed on silica gel using a methylene chloride/methanol gradient to give the free base which was dissolved in methylene chloride, treated with hydrogen chloride gas, and evaporated to give 8.31 g (80%) of the title product.

Workup

  1. customTitle compound was prepared substantially in accordance with the procedure in Example 1E
  2. customThe organic layer was chromatographed on silica gel using a methylene chloride/methanol gradient
  3. customto give the free base which
  4. customevaporated

Sources & evidence

ORD record
ord-696e12bf5b6c43858ca85dcf482c29af
Source dataset
uspto-grants-2003_06
Patent number
US06579871B2

Reaction notes

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