Methanol → HCID 59603006, compound

HRID 1951418Notes

Reaction equation

HRID 1951418 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[Cl: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[Cl: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 59603024HCID 59603024, compound

Product 1

HCID 59603006HCID 59603006, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

245 mg (0.721 mmol) of 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-chlorobenzonitrile are dissolved under an argon atmosphere in 15 ml of abs. dichloromethane, and 273 mg (1.442 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 stirred for a further 2 h. It is then diluted with 20 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 preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 127 mg (47.9% 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 preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-d28859c77b3d40d7b1640f83d401bcd8
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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