ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Cumylamine → 2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)-1H-indole-3-carboxamide

HRID 2068333
ノート
印刷プレビュー

反応式

HRID 2068333 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=[O:20])[NH:18][CH3:19])=[CH:14][C:13]([C:21]2[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=2)[C:24]([OH:26])=O)=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:39]([NH2:48])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCCl.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17]([NH:18][CH3:19])=[O:20])=[CH:14][C:13]([C:21]2[CH:29]=[CH:28][CH:27]=[C:23]([C:24](=[O:26])[NH:48][C:39]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([CH3:41])[CH3:40])[CH:22]=2)=[CH:12][CH:11]=3)=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592338213-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-1H-indol-5-yl)benzoic acid

生成物 1

HCID 592336602-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)-1H-indole-3-carboxamide
収率 70.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-1H-indol-5-yl)benzoic acid (12 mg, 0.031 mmol) and DIPEA (20 μL, 0.115 mmol) in 1,2-dichloroethane (0.5 mL)/DMF (0.1 mL) was added cumylamine (15 μL, 0.10 mmol) and HATU (15 mg, 0.039 mmol). The reaction was stirred at r.t. for 30 min, then the volatiles were evaporated and the residue was purified directly by prep HPLC. Concentration afforded the title compound as a white powder (11 mg, 68% yield). 1H NMR (500 MHz, MeOD) δ ppm 8.52 (s, 1H) 8.09 (d, J=7.93 Hz, 2H) 7.85 (d, J=7.63 Hz, 1H) 7.66-7.77 (m, 3H) 7.49-7.57 (m, 3H) 7.47 (d, J=8.24 Hz, 2H) 7.31 (t, J=7.78 Hz, 2H) 7.23 (t, J=8.85 Hz, 2H) 7.19 (t, J=7.32 Hz, 1H) 2.89 (s, 3H) 1.78 (s, 6H). LC/MS was performed on a Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. LC/MS method: solvent A=10% CH3CN/90% H2O/0.1% TFA, solvent B=90% CH3CN/10% H2O/0.1% TFA, start % B=0, final % B=100, gradient time=3 min, stop time=4 min, flow rate=4 ml/min, column: Sunfire C18 5 μm 4.6×50 mm; HPLC Rt=1.49 min, (ES+) m/z (MH+)=506. Analytical HPLC method: solvent A=5% CH3CN/95% H2O/0.1% TFA, solvent B=95% CH3CN/5% H2O/0.1% TFA, start % B=10, final % B=100, gradient time=15 min, stop time=18 min, flow rate=1 ml/min. Column: Waters Sunfire C-18, 3.5 μm 4.6×150 mm, Rt=15.29 min, purity=97%; column: Waters Xbridge Phenyl 3.5 μm 4.6×150 mm, Rt=11.59 min, purity=98%.

後処理

  1. customthe volatiles were evaporated
  2. customthe residue was purified directly by prep HPLC
  3. concentrationConcentration

出典と根拠

ORDレコード
ord-e270f46b9cb2407bba11523707e4eeec
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08293909B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート