Triacetoxyperiodinane → HCID 89922524, 화합물

HRID 921848노트

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HRID 921848 반응식
[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH2:9][OH:10])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:33][CH2:32]2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH:9]=[O:10])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:32][CH2:33]2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1

참가 물질

4

반응물 2

HCID 159087Triacetoxyperiodinane2회HCID 89922862HCID 89922862, 화합물

생성물 1

HCID 89922524HCID 89922524, 화합물수율 67.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

2-((2-chloro-5-cyano-3-(1-hydroxypropan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (37 mg, 0.070 mmol) was taken up in DCM (1 mL) and the solution was cooled to 0° C. Dess-Martin periodinane (35.6 mg, 0.084 mmol) was added, and the reaction was stirred at 0° C. for 1.5 h. Some SM still remaining, so an additional 0.4 eq. (12 mg) of Dess-Martin was added, and the reaction was stirred for 30 min. The reaction was quenched with 2M K3PO4 and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0%-60% EtOAc/Hex; 12 g column). 2-((2-chloro-5-cyano-3-(1-oxopropan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (25 mg) was obtained as a glassy liquid.

후처리

  1. stirringthe reaction was stirred for 30 min
  2. customThe reaction was quenched with 2M K3PO4
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash column chromatography (0%-60% EtOAc/Hex; 12 g column)

출처 및 근거

ORD 기록
ord-ad29713f89d8402ca0dacc569958619d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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