Oxalyl chloride → HCID 22484122, 화합물

HRID 2181358노트

반응식

HRID 2181358 반응식
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([C:23]([OH:25])=O)=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[S:11][C:5]=2[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]1=[O:30].C(Cl)(=O)[C:32]([Cl:34])=O>ClCCl.CN(C)C=O>[Cl:34][CH2:32][C:23]([C:9]1[C:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:5]=2[S:11][C:10]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:21])([F:22])[F:20])=[O:25]

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 52825261,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]thieno[2,3-d]pyrimidine-5-carboxylic acid

생성물 1

HCID 22484122HCID 22484122, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-5-carboxylic acid, (prepared by the method of Example 8a) (3.665 g) was suspended in dichloromethane (70 ml) containing dimethyl formamide (1 drop) and treated with oxalyl chloride (1.47 ml). 1 hr after gas evolution ceased the reaction was concentrated in vacuo and stored under high vacuum for 1 h. The residue was redissolved in dichloromethane (50 ml) and treated with triethylamine (1 ml). To this solution was added trimethylsilyldiazomethane (7 mls of 2M solution in tetrahydrofuran) and the reaction was stirred at room temperature under an atmosphere of nitrogen for 4 hrs before HCl (8 ml, 4M in dioxane) was added. The reaction was stirred for 18 hrs before being concentrated in vacuo and the residue was purified by chromatography eluting with 2:1 isohexane:diethyl ether. The product was recrystallised from ethyl acetate and isohexane to yield the subtitle compound as white needles(4.616 g)

후처리

  1. custom1 hr
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane (50 ml)
  4. additiontreated with triethylamine (1 ml)
  5. additionTo this solution was added trimethylsilyldiazomethane (7 mls of 2M solution in tetrahydrofuran)
  6. additionwas added
  7. stirringThe reaction was stirred for 18 hrs
  8. concentrationbefore being concentrated in vacuo
  9. customthe residue was purified by chromatography
  10. washeluting with 2:1 isohexane
  11. customThe product was recrystallised from ethyl acetate and isohexane

출처 및 근거

ORD 기록
ord-e878c66bce344e8f8aa5136746291c0c
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06890923B2

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