N,N-Dimethylsulfamide → 13-Cyclohexyl-n-[(dimethylamino)sulfonyl]-6,7-dihydro-(5r,6s)-rel-5,6-dihydroxy-5h-indolo[2,1-a][2]benzazepine-10-carboxamide

HRID 1394877ノート

反応式

HRID 1394877 の反応式
Cl.CN(C)CCCN=C=NCC.[CH:13]1([C:19]2[C:20]3[CH:21]=[CH:22][C:23]([C:39](O)=[O:40])=[CH:24][C:25]=3[N:26]3[CH2:32][C@H:31]([OH:33])[C@H:30]([OH:34])[C:29]4[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=4[C:27]=23)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:42][N:43]([CH3:48])[S:44]([NH2:47])(=[O:46])=[O:45]>CN(C1C=CN=CC=1)C.CN(C=O)C.C(Cl)Cl>[CH:13]1([C:19]2[C:20]3[CH:21]=[CH:22][C:23]([C:39]([NH:47][S:44]([N:43]([CH3:48])[CH3:42])(=[O:46])=[O:45])=[O:40])=[CH:24][C:25]=3[N:26]3[CH2:32][C@H:31]([OH:33])[C@H:30]([OH:34])[C:29]4[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=4[C:27]=23)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

7

反応物 3

HCID 134472N,N-DimethylsulfamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69207235(5R,6S)-rel-13-Cyclohexyl-6,7-dihydro-5,6-dihydroxy-5H-indolo[2,1-a}[2]benzazepine-10-carboxylic acid

生成物 1

HCID 6920646513-Cyclohexyl-n-[(dimethylamino)sulfonyl]-6,7-dihydro-(5r,6s)-rel-5,6-dihydroxy-5h-indolo[2,1-a][2]benzazepine-10-carboxamide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
22 °C

実験手順

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (12.6 mg, 0.066 mmol) was added to a solution of 13-cyclohexyl-6,7-dihydro-(5R,6S)-rel-5,6-dihydroxy-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (8.7 mg, 0.022 mmol) and DMAP (8.1 mg, 0.066 mmol) in DMF (0.3 mL) and CH2Cl2 (0.3 mL) at 22° C. The vial was shaken for a minute at 22° C. then N,N-dimethylsulfamide (5.5 mg, 0.044 mmol) was added. Stirring was continued for 18 hr. The solution was then filtered and purified by Prep. reverse phase chromatography. The product containing fraction was concentrated on a Speed Vac® to leave the title compound as a white film (1.2 mg, 11%). ESI-MS m/z 498 (MH+) 1H NMR (500 MHz, MeOD) δ 1.23-1.33 (m, 1 H) 1.39-1.54 (m, 2 H) 1.62 (m, 1 H) 1.77-1.87 (m, 2 H) 1.93-2.18 (m, 4 H) 2.99 (d, J=11.29 Hz, 1 H) 3.04 (s, 6 H) 3.35 (m, 1 H) 4.42 (d, J=4.58 Hz, 1 H) 4.56 (m, 1 H) 4.75 (dd, J=14.50, 7.17 Hz, 1 H) 7.47 (m, 2 H) 7.54 (m, 1 H) 7.61 (dd, J=8.55, 1.53 Hz, 1 H) 7.80 (d, J=7.63 Hz, 1 H) 7.94 (d, J=8.85 Hz, 1 H) 8.13 (s, 1 H).

後処理

  1. stirringStirring
  2. filtrationThe solution was then filtered
  3. custompurified by Prep
  4. additionThe product containing fraction
  5. concentrationwas concentrated on a Speed Vac®

出典と根拠

ORDレコード
ord-59a4257acb344c26b443cad0999e6bfc
出典データセット
uspto-grants-2008_03
特許番号
US07348425B2

反応ノート

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