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

Diisopropylethylamine → (3R)-N-[1-(2-Amino-pyrimidin-4-yl)-piperidin-4-yl]-3-[(2-chloro-benzoyl)amino]-N-methyl-2,3-dihydro-1H-indene-5-carboxylic acid amide

HRID 1193426
ノート
印刷プレビュー

反応式

HRID 1193426 の反応式
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C@H:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([N:18]([CH3:25])[CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[O:17])[CH:14]=2)[CH2:9][CH2:8]1)=[O:5].Cl[C:31]1[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[N:32]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[NH2:37][C:33]1[N:34]=[C:35]([N:22]2[CH2:21][CH2:20][CH:19]([N:18]([CH3:25])[C:16]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[CH2:9][CH2:8][C@H:7]4[NH:6][C:4](=[O:5])[C:3]3[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=3[Cl:1])=[O:17])[CH2:24][CH2:23]2)[CH:36]=[CH:31][N:32]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2233322-Amino-4-chloropyrimidineHCID 66798745(R)-3-(2-chlorobenzamido)-N-methyl-N-(piperidin-4-yl)-2,3-dihydro-1H-indene-5-carboxamide

生成物 1

HCID 66798873(3R)-N-[1-(2-Amino-pyrimidin-4-yl)-piperidin-4-yl]-3-[(2-chloro-benzoyl)amino]-N-methyl-2,3-dihydro-1H-indene-5-carboxylic acid amide収率 45%

試薬・触媒・溶媒 1

HCID 31275
1,4-Dioxane
溶媒

実験手順

A mixture of (R)-3-(2-chlorobenzamido)-N-methyl-N-(piperidin-4-yl)-2,3-dihydro-1H-indene-5-carboxamide (stage 2H-214) (200 mg, 0.486 mmol, 1.0 eq), 4-chloro-pyrimidin-2-ylamine (94 mg, 0.728 mmol, 1.5 eq) and DIPEA (0.125 ml, 0.728 mmol, 1.5 eq) in dioxane (10 ml) was refluxed for 16 h. When the reaction was complete according to TLC monitoring, concentration under reduced pressure was carried out, and the reside was taken up in dichloromethane (50 ml) and washed with water (30 ml) and saturated sodium chloride solution (30 ml). The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 6% methanol in dichloromethane). Yield: 45% (110 mg, 0.267 mmol) Analytical Data—Single Substances Method 1: Equipment and methods for HPLC-MS analysis: HPLC: Waters Alliance 2795 with PDA Waters 2998; MS: Micromass Quattro Micro™ API; column: Waters Atlantis® T3, 3 μm, 100 Å, 2.1×30 mm; column temperature: 40° C., eluent A: purified water+0.1% formic acid; eluent B: acetonitrile (gradient grade)+0.1% formic acid; gradient: 0% B to 100% B in 8.8 min, 100% B for 0.4 min, 100% B to 0% B in 0.01 min, 0% B for 0.8 min; flow: 1.0 ml/min; ionization: ES+, 25 V; batch: 100 μl/min 70% methanol+0.2% formic acid; UV: 200-400 nm.

後処理

  1. temperaturewas refluxed for 16 h
  2. concentrationWhen the reaction was complete according to TLC monitoring, concentration under reduced pressure
  3. washwashed with water (30 ml) and saturated sodium chloride solution (30 ml)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, 6% methanol in dichloromethane)
  7. customcolumn temperature: 40° C., eluent A: purified water+0.1% formic acid
  8. wait100% B for 0.4 min
  9. wait100% B to 0% B in 0.01 min
  10. wait0% B for 0.8 min

出典と根拠

ORDレコード
ord-f59ae764db5145eabc4608e55837563c
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680159B2

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