1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86588100, compound

HRID 1828444Notes

Reaction equation

HRID 1828444 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]2[CH:31]=[CH:30][N:16]3[C:17](=[O:29])[C:18]([CH:27]=O)=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=[C:15]3[CH:14]=2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].FC(F)(F)COP([CH2:46][C:47]([O:49][CH3:50])=[O:48])(=O)OCC(F)(F)F.N12CCCN=C1CCCCC2>O1CCCC1>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]2[CH:31]=[CH:30][N:16]3[C:17](=[O:29])[C:18](/[CH:27]=[CH:46]/[C:47]([O:49][CH3:50])=[O:48])=[C:19]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[N:20]=[C:15]3[CH:14]=2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 184894Nsc 6341372×HCID 433294Lithium ChlorideHCID 22063733HCID 22063733, compound

Product 1

HCID 86588100HCID 86588100, compoundYield 131.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N8-[4-(tert-Butyl)-1,3-thiazol-2-yl]-3-formyl-2-morpholino-4-oxo-4H-pyrido-[1,2-a]pyrimidine-8-carboxamide (98.2 mg, 0.223 mmol) was added with tetrahydrofuran (6 ml), lithium chloride (30 mg, 0.669 mmol) and bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)-phosphonate (142 μl, 0.669 mmol), then added dropwise with 1,8-diazabicyclo[5.4.0]undec-7-ene (92 μl, 0.669 mmol) at room temperature, stirred at room temperature for 1 hour, and further added with bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)-phosphonate (75 μl) and 1,8-diazabicyclo[5.4.0]undec-7-ene (45 μl). The reaction solution was further stirred at room temperature for 30 minutes and concentrated under reduced pressure. The resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1) to obtain 145.8 mg of the title compound in a mixture with 1,8-diazabicyclo[5.4.0]undec-7-ene.

Workup

  1. stirringThe reaction solution was further stirred at room temperature for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-0d7e027e6050474281cbe0e63c29c445
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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