Methanol → 4-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

HRID 1951421

반응식

HRID 1951421 반응식
[C:1]([C:4]1[CH:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]#[N:25])=[CH:16][CH:15]=2)[C:12]2[C:11](=[O:26])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2].ClCCl.F[B-](F)(F)F.[CH2:36]([O+](CC)CC)[CH3:37].CO>O>[C:1]([C:4]1[CH:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]#[N:25])=[CH:16][CH:15]=2)[C:12]2[C:7](=[CH:8][CH:9]=[N:10][C:11]=2[O:26][CH2:36][CH3:37])[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 887MethanolHCID 6344DichloromethaneHCID 2723982Triethyloxonium tetrafluoroborateHCID 596030254-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

생성물 1

HCID 236279894-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

93 mg (0.262 mmol) of 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-1-naphthonitrile are dissolved under an argon atmosphere in 5 ml of abs. dichloromethane, and 99.4 mg (0.268 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 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). 60 mg (59.8% of theory) of the title compound are obtained.

후처리

  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)

출처 및 근거

ORD 기록
ord-fe52c5d155c844f0a03dcff3b06b4614
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404709B2

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