Tetrabutylammonium Fluoride → (Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one

HRID 20692노트

반응식

HRID 20692 반응식
[Si]([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][O:13][C:14]1[C:15]([O:34][CH3:35])=[CH:16][CH:17]=[C:18]2[C:23]=1[O:22][C:21](=[O:24])[CH:20]=[C:19]2[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=1[Cl:33])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[Cl:33][C:27]1[CH:28]=[N:29][CH:30]=[C:31]([Cl:32])[C:26]=1[NH:25][C:19]1[C:18]2[C:23](=[C:14]([O:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][OH:8])[C:15]([O:34][CH3:35])=[CH:16][CH:17]=2)[O:22][C:21](=[O:24])[CH:20]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86618136HCID 86618136, 화합물

생성물 1

HCID 24849220(Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of (Z)-8-(4-(tert-butyldimethylsilyloxy)but-2-enyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one and TBAF (2 mL, 2M THF) was maintained at rt for 18 h, poured into water, and then extracted with EtOAc. The extract was dried, filtered, concentrated, and purified by reverse-phase HPLC (25→100% MeCN/H2O) to give (Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, CD3OD-d6): δ 8.71 (s, 2H), 7.85 (d, 1H), 7.18 (d, 1H), 7.83 (m, 2H), 4.77 (m, 3H), 4.15 (d, 2H), 4.01 (s, 3H); MS (ESI): 422.8.

후처리

  1. extractionextracted with EtOAc
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (25→100% MeCN/H2O)

출처 및 근거

ORD 기록
ord-ac62aebc72e9427e9373a00eff9e5822
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745646B2

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