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

Pyridine → N,N-Dimethyl-5-[3-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-5-[(4-methyl-1,3-thiazol-2-yl)carbamoyl]phenoxy]pyrazine-2-carboxamide

HRID 600528
ノート
印刷プレビュー

反応式

HRID 600528 の反応式
ClC(N(C)C)=C(C)C.[CH3:9][N:10]([CH3:37])[C:11]([C:13]1[N:14]=[CH:15][C:16]([O:19][C:20]2[CH:21]=[C:22]([CH:26]=[C:27]([O:29][C@H:30]3[CH2:34][CH2:33][N:32]([CH3:35])[C:31]3=[O:36])[CH:28]=2)[C:23]([OH:25])=O)=[N:17][CH:18]=1)=[O:12].[CH3:38][C:39]1[N:40]=[C:41]([NH2:44])[S:42][CH:43]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:37][N:10]([CH3:9])[C:11]([C:13]1[CH:18]=[N:17][C:16]([O:19][C:20]2[CH:21]=[C:22]([C:23](=[O:25])[NH:44][C:41]3[S:42][CH:43]=[C:39]([CH3:38])[N:40]=3)[CH:26]=[C:27]([O:29][C@H:30]3[CH2:34][CH2:33][N:32]([CH3:35])[C:31]3=[O:36])[CH:28]=2)=[CH:15][N:14]=1)=[O:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 741432-Amino-4-methylthiazoleHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 59761148HCID 59761148、化合物2 回

生成物 1

HCID 24951579N,N-Dimethyl-5-[3-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-5-[(4-methyl-1,3-thiazol-2-yl)carbamoyl]phenoxy]pyrazine-2-carboxamide収率 45%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-Chloro-N,N,2-trimethyl-prop-1-en-1-amine (0.14 mL, 1.1 mmol) was added to a solution of 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid (Intermediate 45) (358 mg, 0.9 mmol) in DCM (7 mL) and stirred at ambient temperature for 30 minutes. 4-Methyl-1,3-thiazol-2-amine (CAS no. 1603-91-4) (206 mg, 1.8 mmol) and pyridine (0.15 mL, 1.8 mmol) were added and the reaction stirred for 20 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (30 mL), washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica eluting with a gradient of 0 to 5% methanol in DCM to afford the product (200 mg, 45%). 1H NMR δ (300 MHz, CDCl3) 2.09-2.22 (m, 1H), 2.25 (s, 3H), 2.50-2.65 (m, 1H), 2.93 (s, 3H), 3.18 (d, 6H), 3.34-3.55 (m, 2H), 4.86 (t, 1H), 6.56 (s, 1H), 7.16 (s, 1H), 7.37 (s, 1H), 7.54 (s, 1H), 8.37 (s, 1H), 8.51 (s, 1H), 10.0-11.0 (br s, 1H); m/z 497 (M+H+).

後処理

  1. stirringthe reaction stirred for 20 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  4. washwashed with water (2×10 mL) and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica eluting with a gradient of 0 to 5% methanol in DCM

出典と根拠

ORDレコード
ord-24428df036bc48f1b7df6fb1ed858bb5
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902200B2

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