1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86760385, compound

HRID 348444Notes

Reaction equation

HRID 348444 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14](S(C)=O)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:28][C:29]([CH3:34])=[CH:30][C:31]=2CO)=[CH:23][CH:22]=1.C1CCN2C(=NCCC2)CC1.[C:46](OCC)(=[O:48])C.CCCCCC>C1COCC1.ClCCl.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([O:48][CH2:46][C:30]3[CH:31]=[C:27]([C:24]4[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][CH:25]=4)[O:28][C:29]=3[CH3:34])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21087366HCID 21087366, compoundHCID 21226206Ethyl acetate hexaneHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 86760385HCID 86760385, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (60 mg, 0.215 mmol) in THF (1 mL) was added [2-(4-chlorophenyl)-5-methylfuran-3-yl]methanol (96 mg, 0.43 mmol) followed by DBU (65 μL, 0.43 mmol). The reaction was stirred for 1 h, diluted with 50% dichloromethane/hexane, and passed through a plug of SiO2 washing with 30% ethyl acetate/hexane. The filtrate was concentrated in vacuo, and the resulting solids were triturated with 20% ethyl acetate/hexane to afford 44.5 mg (47% yield) of the titled product as a white solid. ESI-MS m/z 438 (MH+) and 440 (M+2)H+, 436 (M−H)− and 438 ((M+2)−H)−.

Workup

  1. concentrationThe filtrate was concentrated in vacuo
  2. customthe resulting solids were triturated with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-82214c0e0d1549699f23fe6ef0fed266
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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