Diethyl Pyrocarbonate → 2-Methyl-N-((1R,2S)-2-{[(3aR,4S,9bR)-4-propyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)-1H-benzimidazole-5-carboxamide

HRID 550305ノート

反応式

HRID 550305 の反応式
Cl.[CH2:2]([C@@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH2:26])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1)[CH2:3][CH3:4].[CH3:27][C:28]1[NH:32][C:31]2[CH:33]=[CH:34][C:35]([C:37](O)=[O:38])=[CH:36][C:30]=2[N:29]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O>CN(C=O)C.O>[CH3:27][C:28]1[NH:32][C:31]2[CH:33]=[CH:34][C:35]([C:37]([NH:26][C@@H:21]3[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]3[C:18]([N:17]3[C@@H:13]4[C@@H:14]([C@H:5]([CH2:2][CH2:3][CH3:4])[NH:6][C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=54)[CH2:15][CH2:16]3)=[O:19])=[O:38])=[CH:36][C:30]=2[N:29]=1

参加物

7

反応物 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 11326092-methyl-1H-benzimidazole-5-carboxylic acidHCID 67150467(1R,2S)-2-{[(3aR,4R,9bR)-4-(propyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride

生成物 1

HCID 1784481662-Methyl-N-((1R,2S)-2-{[(3aR,4S,9bR)-4-propyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)-1H-benzimidazole-5-carboxamide収率 47%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of (1R,2S)-2-{[(3aR,4R,9bR)-4-(propyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (203 mg, 0.490 mmol) in DMF (4 ml) were added 2-methyl-1H-benzimidazole-5-carboxylic acid (86.2 mg, 0.490 mmol), triethylamine (0.206 ml, 1.47 mmol) and DEPC (0.0812 ml, 0.490 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 hrs. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous MgSO4, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel and eluted with ethyl acetate-methanol (1:0-9:1) to give the title compound (115 mg, 47%) as an amorphous form.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate-methanol (1:0-9:1)

出典と根拠

ORDレコード
ord-2bdb27f2e99346ba8acdf3075fb13851
出典データセット
uspto-grants-2011_05
特許番号
US07943770B2

反応ノート

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