Morpholine → methyl 2-(2-acetylphenyl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1453363ノート

反応式

HRID 1453363 の反応式
[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3CC=C[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:22]1[C:32]2C3=CC4C=CC(C(O)=O)=CC=4N3C=CC[C:26]=2[CH:25]=[CH:24][CH:23]=1.C1C2C3=CC4C=C[C:58]([C:61](O)=[O:62])=CC=4N3CC(C(O)=O)=CC=2C=CC=1.[CH3:67]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.N1CCOCC1>CS(C)=O>[C:61]([C:5]1[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=1[C:10]1[NH:9][C:18]2[C:13]([C:12]=1[CH:22]1[CH2:32][CH2:26][CH2:25][CH2:24][CH2:23]1)=[CH:14][CH:15]=[C:16]([C:19]([O:21][CH3:67])=[O:20])[CH:17]=2)(=[O:62])[CH3:58]

参加物

8

反応物 6

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 665887027H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylic acidHCID 666396797H-indolo[2,1-a][2]benzazepine-10-carboxylic acidHCID 685639665H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

生成物 1

HCID 58765163methyl 2-(2-acetylphenyl)-3-cyclohexyl-1H-indole-6-carboxylate収率 82%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-5-methyl-6-(4-morpholinylcarbonyl)-, methyl ester. To a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylic acid, 13-cyclohexyl-5-methyl-, 10-methyl ester (120 mg, 0.28 mmol) in DMSO (3.0 mL), TBTU (135 mg, 0.42 mmol) and DIPEA (0.244 mL, 1.4 mmol) were added. The reaction mixture was stirred at rt for 15 min. Then morpholine (0.037 mL, 0. 42 mmol) was added and the reaction mixture was stirred at rt for overnight. It was then concentrated under reduced pressure and the residue was purified by Prep. reverse phase HPLC to give the title compound as a white solid, (115 mg, 82% yield). MS m/z 499(MH+); 1H NMR (500 MHz, CD3OD) δ ppm Compound exists as a complex mixture of rotamers.

後処理

  1. stirringthe reaction mixture was stirred at rt for overnight
  2. concentrationIt was then concentrated under reduced pressure
  3. customthe residue was purified by Prep

出典と根拠

ORDレコード
ord-8a9357df51444150a0e12e23db425a44
出典データセット
uspto-grants-2009_01
特許番号
US07473688B2

反応ノート

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