Methanol → HCID 59603036, compound

HRID 1951417Notes

Reaction equation

HRID 1951417 reaction equation
[C:1]([C:4]1[CH:13]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[F:22])[C:12]2[C:11](=[O:23])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:24])(=[O:3])[CH3:2].ClCCl.F[B-](F)(F)F.[CH2:33]([O+](CC)CC)[CH3:34].CO>O>[C:1]([C:4]1[CH:13]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[F:22])[C:12]2[C:7](=[CH:8][CH:9]=[N:10][C:11]=2[O:23][CH2:33][CH3:34])[NH:6][C:5]=1[CH3:24])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 2723982Triethyloxonium tetrafluoroborateHCID 59603035HCID 59603035, compound

Product 1

HCID 59603036HCID 59603036, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

18 mg (0.056 mmol) of 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-fluorobenzonitrile are dissolved under an argon atmosphere in 5 ml abs. dichloromethane, and 21.2 mg (0.111 mmol) of triethyloxonium tetrafluoroborate are added. After a reaction time of two hours at room temperature (reaction checked by HPLC), the mixture is mixed with 5 ml of methanol and 0.5 ml of water and again stirred for 2 h. It is then diluted with 10 ml of water and extracted three times with dichloromethane. The combined organic phases are dried with sodium sulfate, and the solvent is removed in a rotary evaporator. The residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 3:7). 7 mg (35.4% of theory) of the title compound are obtained.

Workup

  1. customAfter a reaction time of two hours at room temperature (reaction checked by HPLC)
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic phases are dried with sodium sulfate
  4. customthe solvent is removed in a rotary evaporator
  5. customThe residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 3:7)

Sources & evidence

ORD record
ord-0e90016625ea4f98be4f617c694e02b7
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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