Tetrahydrofuran → HCID 178439806, compound

HRID 1828493Notes

Reaction equation

HRID 1828493 reaction equation
C([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:32]=[C:31](/[CH:33]=[CH:34]/[C:35]4[S:36][CH:37]=[C:38]([CH:40]([CH3:42])[CH3:41])[N:39]=4)[CH:30]=[CH:29][N:14]3[C:15](=[O:28])[C:16]=2/[CH:17]=[CH:18]/[C:19]2[N:23](CCC#N)[N:22]=[N:21][N:20]=2)[CH2:6]1)(=O)C.O1CCCC1.C[O-].[Na+].[Cl-].[NH4+]>CO>[OH:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:32]=[C:31](/[CH:33]=[CH:34]/[C:35]4[S:36][CH:37]=[C:38]([CH:40]([CH3:42])[CH3:41])[N:39]=4)[CH:30]=[CH:29][N:14]3[C:15](=[O:28])[C:16]=2/[CH:17]=[CH:18]/[C:19]2[NH:20][N:21]=[N:22][N:23]=2)[CH2:6]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide2×HCID 86588123HCID 86588123, compound2×

Product 1

HCID 178439806HCID 178439806, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 1-(3-{(E)-2-[1-(2-cyanoethyl)-1H-1,2,3,4-tetraazol-5-yl]-1-ethenyl}-8[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)3-piperidyl acetate (25.9 mg, 0.0442 mmol) obtained in (C) was suspended in methanol (0.5 ml) and anhydrous tetrahydrofuran (1.0 ml), added with sodium methoxide (4.8 mg, 0.0884 mmol) under ice cooling, and then stirred for 4 hours. The reaction solution was further added with sodium methoxide (4.8 mg, 0.0884 mmol) and stirred for 1 hour. The reaction mixture was added with saturated aqueous ammonium chloride and extracted with chloroform, and the organic layer was dried over magnesium sulfate. Then, the solvent was evaporated under reduced pressure, and the residue was purified by thin layer chromatography (chloroform:methanol=10:1, v/v) to obtain the title compound (12.7 mg, 59%).

Workup

  1. stirringstirred for 1 hour
  2. extractionextracted with chloroform
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customThen, the solvent was evaporated under reduced pressure
  5. customthe residue was purified by thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-3445b28743c0418cbbf5178268e6b3bf
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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