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 1476527ノート

反応式

HRID 1476527 の反応式
[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]

参加物

5

反応物 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)-dione2 回HCID 672590924-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9555484c3a5b416da47d576095bab4ab
出典データセット
uspto-grants-2015_04
特許番号
US09018175B2

反応ノート

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