Acetic Acid → HCID 178482798, compound

HRID 2236786Notes

Reaction equation

HRID 2236786 reaction equation
N[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7]/[CH:8]=[C:9]2\[C:10](=[O:21])[NH:11][C:12](=[O:20])[C:13]3[C:18]\2=[CH:17][C:16]([I:19])=[CH:15][CH:14]=3)=[CH:4][C:3]=1[O:24][Si](C(C)C)(C(C)C)C(C)C.[C:35]([BH3-])#[N:36].[Na+].[C:39](O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.CO>[CH3:39][N:36]([CH3:35])[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7]/[CH:8]=[C:9]2\[C:10](=[O:21])[NH:11][C:12](=[O:20])[C:13]3[C:18]\2=[CH:17][C:16]([I:19])=[CH:15][CH:14]=3)=[CH:4][C:3]=1[OH:24]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 5003444Sodium cyanoborohydrideHCID 178460972HCID 178460972, compound

Product 1

HCID 178482798HCID 178482798, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

An amount of 300 mg (0.51 mmol) of (4Z)-4-[({4-amino-3-[(triisopropylsilyl)oxy]benzyl}amino)methylene]-6-iodoisoquinoline-1,3(2H,4H)-dione and formylaldehyde (45.9 mg, 1.53 mmol) were dissolved in tetrahydrofuran (3 mL) and methanol (2 mL). After stirring for ten minutes, a mixture of sodium cyanoborohydride (64.1 mg, 1.02 mmol) and acetic acid (0.4 mL, 5.1 mmol) were added drop-wise. The mixture is allowed to stir for 2.5 hours. Tetrabutylammonium fluoride (2 mL) is added and stirred for additional 1 hour. The mixture is neutralized with 1 NHCl solution and extracted with dichloromethane (200 ml), dried over sodium sulfate and evaporated. The desired final product is purified by column chromatography to afford 60 mg (26% yield) of a light brown solid.; mp 198-199° C.

Workup

  1. additionwere added drop-wise
  2. stirringto stir for 2.5 hours
  3. stirringstirred for additional 1 hour
  4. extractionextracted with dichloromethane (200 ml)
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe desired final product is purified by column chromatography

Sources & evidence

ORD record
ord-dbe80ba940664e559432d4e304d485e7
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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