Acetic Acid → HCID 86679288, compound

HRID 1519729Notes

Reaction equation

HRID 1519729 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]([C:31]#[C:32]/[CH:33]=[CH: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]([C:31]#[C:32]/[CH:33]=[CH: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 triacetoxyborohydride2×HCID 86679289HCID 86679289, compound

Product 1

HCID 86679288HCID 86679288, compoundYield 91%

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-[(3E)-4-(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)but-3-en-1-yn-1-yl]benzene (0.20 g) as obtained in Example 22-(3), and the mixture was stirred for 1 hour and 15 minutes at room temperature. Sodium triacetoxyborohydride (0.10 g) was added, and the mixture was stirred for 1.5 hours at room temperature. Water and chloroform were added, and the organic layer was isolated. The extract was dried over anhydrous sodium sulfate, and the desiccant was filtered out. The solvent was distilled off under reduced pressure to obtain 1-[(cyclopropylamino)methyl]-4-[(3E)-4-(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)but-3-en-1-yn-1-yl]benzene (orange oil) (0.20 g, 91%).

Workup

  1. customas obtained in Example 22-(3)
  2. stirringthe mixture was stirred for 1.5 hours at room temperature
  3. customthe organic layer was isolated
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationthe desiccant was filtered out
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-de2faab02396427fab4ff477118d007b
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

Loading…