Acetic Acid → HCID 86679293, compound

HRID 1519734Notes

Reaction equation

HRID 1519734 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:23]([C:25]1[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]#[C:34][C:35]2[CH:40]=[CH:39][C:38]([C:41](=[O:53])[N:42]([CH:44]([C:49]([NH:51][CH3:52])=[O:50])[C:45]([O:47][CH3:48])=[O:46])[CH3:43])=[CH:37][CH:36]=2)=[CH:27][CH:26]=1)=O>C(Cl)(Cl)Cl.O>[CH:1]1([NH:4][CH2:23][C:25]2[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]#[C:34][C:35]3[CH:40]=[CH:39][C:38]([C:41](=[O:53])[N:42]([CH:44]([C:49]([NH:51][CH3:52])=[O:50])[C:45]([O:47][CH3:48])=[O:46])[CH3:43])=[CH:37][CH:36]=3)=[CH:27][CH:26]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydride3×HCID 86679292HCID 86679292, compound

Product 1

HCID 86679293HCID 86679293, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

Cyclopropylamine (99 μL), acetic acid (27 μL) and sodium triacetoxyborohydride (0.10 g) were added to a chloroform (4.0 mL) suspension of 1-formyl-4-[(1E)-4-(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)but-1-en-3-yn-1-yl]benzene (0.20 g) as obtained in Example 23-(3), and the mixture was stirred for 1 hour and 10 minutes at room temperature. Sodium triacetoxyborohydride (0.10 g) was added, and the mixture was stirred for 1 hour and 15 minutes at room temperature. Further, sodium triacetoxyborohydride (0.10 g) was added, and the mixture was stirred for 1 hour and 15 minutes at room temperature. Water and chloroform were added to isolate the organic layer, and the extract was washed with water and brine sequentially. The washed extract was dried over anhydrous sodium sulfate, and the desiccant was filtered out. Then, the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=50/1→10/1) to obtain 1-[(cyclopropylamino)methyl]-4-[(1E)-4-(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)but-1-en-3-yn-1-yl]benzene (orange oil) (0.18 g, 83%).

Workup

  1. customas obtained in Example 23-(3)
  2. stirringthe mixture was stirred for 1 hour and 15 minutes at room temperature
  3. stirringthe mixture was stirred for 1 hour and 15 minutes at room temperature
  4. customto isolate the organic layer
  5. washthe extract was washed with water and brine sequentially
  6. extractionThe washed extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationthe desiccant was filtered out
  9. distillationThen, the solvent was distilled off under reduced pressure
  10. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=50/1→10/1)

Sources & evidence

ORD record
ord-e2372ba359474f26a4995ac28df88a18
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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