Diisopropylethylamine → 3-[1-({4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]phenyl}carbonyl)piperidin-4-yl]-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-6-phenylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

HRID 1476527노트

반응식

HRID 1476527 반응식
[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:11]2[C:10]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=3)=[N:9][C@@H:8]3[CH2:25][CH2:26][S:27][CH2:28][C@@H:7]3[C:6]=2[CH:5]=1)[CH3:2].CCN(C(C)C)C(C)C.[CH2:38]([N:40]1[N:44]=[N:43][C:42]([CH2:45][N:46]2[C:51]3[CH:52]=[C:53]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[S:54][C:50]=3[C:49](=[O:61])[N:48]([CH:62]3[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]3)[C:47]2=[O:68])=[N:41]1)[CH3:39]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:11]2[C:10]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([N:65]4[CH2:66][CH2:67][CH:62]([N:48]5[C:49](=[O:61])[C:50]6[S:54][C:53]([C:55]7[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=7)=[CH:52][C:51]=6[N:46]([CH2:45][C:42]6[N:43]=[N:44][N:40]([CH2:38][CH3:39])[N:41]=6)[C:47]5=[O:68])[CH2:63][CH2:64]4)=[O:22])=[CH:23][CH:24]=3)=[N:9][C@@H:8]3[CH2:25][CH2:26][S:27][CH2:28][C@@H:7]3[C:6]=2[CH:5]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 672587131-[(2-ethyl-2H-tetrazol-5-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione2회HCID 672590924-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid

생성물 1

HCID 532354993-[1-({4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]phenyl}carbonyl)piperidin-4-yl]-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-6-phenylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (160 mg; compound C10) dissolved in DCM (20 ml) HBTU (167 mg) and DIPEA (0.21 ml) are added and the reaction mixture is stirred for 30 min at RT. Subsequently, 1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione (175 mg; compound B39) is added and the reaction mixture is stirred for 24 h at RT. After extraction with a saturated solution of sodium hydrogen carbonate and a saturated solution of sodium chloride the organic phase is separated and dried over Na2SO4. After filtration the solvent is removed under reduced pressure to give the crude title product. After purification by flash column chromatography (silica gel, eluent: EtOAc) the title compound is obtained as a solid.

후처리

  1. stirringthe reaction mixture is stirred for 24 h at RT
  2. extractionAfter extraction with a saturated solution of sodium hydrogen carbonate
  3. customa saturated solution of sodium chloride the organic phase is separated
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customis removed under reduced pressure

출처 및 근거

ORD 기록
ord-9555484c3a5b416da47d576095bab4ab
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018175B2

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