1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53246993、化合物

HRID 1476534ノート

反応式

HRID 1476534 の反応式
FC(F)(F)C(O)=O.[CH2:8]([N:10]1[N:14]=[C:13]([CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:24][C:20]=3[C:19](=[O:31])[N:18]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:17]2=[O:38])[CH:12]=[N:11]1)[CH3:9].[CH2:39]([O:41][C:42]1[C:51]([O:52][CH3:53])=[CH:50][C:49]2[C:48]([C:54]3[CH:62]=[CH:61][C:57]([C:58](O)=[O:59])=[CH:56][CH:55]=3)=[N:47][C@@H:46]3[CH2:63][CH2:64][S:65][CH2:66][C@@H:45]3[C:44]=2[CH:43]=1)[CH3:40].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl.O>[CH2:39]([O:41][C:42]1[C:51]([O:52][CH3:53])=[CH:50][C:49]2[C:48]([C:54]3[CH:55]=[CH:56][C:57]([C:58]([N:35]4[CH2:36][CH2:37][CH:32]([N:18]5[C:19](=[O:31])[C:20]6[S:24][C:23]([C:25]7[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=7)=[CH:22][C:21]=6[N:16]([CH2:15][C:13]6[CH:12]=[N:11][N:10]([CH2:8][CH3:9])[N:14]=6)[C:17]5=[O:38])[CH2:33][CH2:34]4)=[O:59])=[CH:61][CH:62]=3)=[N:47][C@@H:46]3[CH2:63][CH2:64][S:65][CH2:66][C@@H:45]3[C:44]=2[CH:43]=1)[CH3:40]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516920Potassium bisulfateHCID 27960291-Hydroxybenzotriazole hydrateHCID 67259075HCID 67259075、化合物2 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 53246993HCID 53246993、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 1-[(2-ethyl-2H-1,2,3-triazol-4-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione trifluoroacetate (300 mg; compound B45), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (217 mg; compound C10), EDCI (104 mg) and HOBT hydrate (74 mg) in DCM (10 ml) DIPEA (0.24 ml) is added. After 14 h at RT water and aqueous potassium hydrogen sulfate solution (10% w/w) are added and the mixture is extracted with DCM. The combined organic layers are dried (sodium sulfate) and concentrated under reduced pressure. The residue is purified by twofold flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 1/0 to 1/1 (v/v)] and preparative HPLC to afford the title compound as a solid.

後処理

  1. additionis added
  2. extractionthe mixture is extracted with DCM
  3. dry with materialThe combined organic layers are dried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by twofold flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 1/0 to 1/1 (v/v)] and preparative HPLC

出典と根拠

ORDレコード
ord-a68a85cc6c574dcea9b73e202d56c6a9
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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