Sodium Carbonate → N-{1-[(5-Amino-1,3,4-oxadiazol-2-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178428Notes

Reaction equation

HRID 1178428 reaction equation
O1CCOCC1.[Cl:7][C:8]1[S:34][C:11]2[NH:12][C:13]([C:15]([NH:17][CH:18]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:28][C:29]([NH:31][NH2:32])=[O:30])[C:19]3=[O:33])=[O:16])=[CH:14][C:10]=2[CH:9]=1.[N:35]#[C:36]Br.C([O-])([O-])=O.[Na+].[Na+]>O.CCOC(C)=O.C1COCC1>[NH2:35][C:36]1[O:30][C:29]([CH2:28][N:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:27][CH:18]([NH:17][C:15]([C:13]3[NH:12][C:11]4[S:34][C:8]([Cl:7])=[CH:9][C:10]=4[CH:14]=3)=[O:16])[C:19]2=[O:33])=[N:31][N:32]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 312751,4-Dioxane2×HCID 587218262-chloro-N-[1-(2-hydrazino-2-oxoethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 10026388N-{1-[(5-Amino-1,3,4-oxadiazol-2-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 20%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,4-Dioxane (5 mL), 2-chloro-N-[1-(2-hydrazino-2-oxoethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 15; 300 mg, 0.72 mmol), cyanogen bromide (80 mg, 0.75 mmol) and 1,4-dioxane (2 mL) were added to a solution of Na2CO3 (77 mg, 0.72 mmol) in H2O (1.7 mL) and stirred for 18 hours. The mixture was diluted with EtOAc (50 mL) and THF (20 mL) and washed with H2O (25 mL). The organic was dried (Na2SO4), filtered and evaporated. The residue was purified by reverse phase column chromatography to give a brown solid. This was triturated with refluxing Et2O (25 mL), filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford the title compound (63 mg, 20%) as a brown powder.

Workup

  1. washwashed with H2O (25 mL)
  2. dry with materialThe organic was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by reverse phase column chromatography
  6. customto give a brown solid
  7. customThis was triturated with refluxing Et2O (25 mL)
  8. filtrationfiltered
  9. washwashed with Et2O (25 mL)

Sources & evidence

ORD record
ord-9e4c01fc64a2470196c0f002b0f328eb
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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