Cyanoacetic acid → HCID 71264074, compound

HRID 1506263Notes

Reaction equation

HRID 1506263 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][NH:5][CH2:4][C@@H:3]1[N:8]1[C:13]2[C:14]3[CH:20]=[CH:19][NH:18][C:15]=3[N:16]=[CH:17][C:12]=2[CH2:11][O:10][CH2:9]1.[C:21]([CH2:23][C:24](O)=[O:25])#[N:22].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(Cl)(Cl)Cl.CO.O>[CH3:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:24](=[O:25])[CH2:23][C:21]#[N:22])[CH2:4][C@@H:3]1[N:8]1[C:13]2[C:14]3[CH:20]=[CH:19][NH:18][C:15]=3[N:16]=[CH:17][C:12]=2[CH2:11][O:10][CH2:9]1

Participants

8

Reactant 4

HCID 9740Cyanoacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71258513HCID 71258513, compound

Product 1

HCID 71264074HCID 71264074, compoundYield 11.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

rac-1-[(3R,4R)-4-Methylpiperidin-3-yl]-1,2,4,7-tetrahydropyrrolo[3′,2′:5,6]pyrido[4,3-d][1,3]oxazine (21.2 mg, 0.0777 mmol) in N,N-dimethylformamide was stirred with cyanoacetic acid (15 mg, 0.18 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (67 mg, 0.18 mmol), N,N-diisopropylethylamine (44.9 μL, 0.264 mmol) at room temperature for one day. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Hi Flash column amino type manufactured by Yamazen Corporation: chloroform/methanol=20/1 (v/v)) to give the title compound as a yellow oil (3 mg, yield 10%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (Hi Flash column amino type

Sources & evidence

ORD record
ord-be334cf04f2c4e2a97e195b83c8ddc6b
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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