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

Water → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((6-fluoro-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl)-N2-methylpyrimidine-2,4-diamine

HRID 2409078
ノート
印刷プレビュー

反応式

HRID 2409078 の反応式
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH2:18][C:19]4[N:24]=[C:23]5[CH:25]=[CH:26][N:27](COCC[Si](C)(C)C)[C:22]5=[CH:21][C:20]=4[F:36])[CH3:17])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.[NH4+].[OH-]>C1COCC1>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH2:18][C:19]4[N:24]=[C:23]5[CH:25]=[CH:26][NH:27][C:22]5=[CH:21][C:20]=4[F:36])[CH3:17])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1
参加物反応条件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 962WaterHCID 14923Ammonium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 86762628N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl)-N2-methylpyrimidine-2,4-diamine

生成物 1

HCID 71600008N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((6-fluoro-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl)-N2-methylpyrimidine-2,4-diamine
収率 20%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
63 °C

実験手順

A mixture of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl)-N2-methylpyrimidine-2,4-diamine (40 mg, 0.1 mmol) and tetrabutyl ammonium fluoride (260 mg, 1 mmol) in THF (5 mL) was heated at 63° C. for 18 h. The reaction mixture was poured into water (10 mL) and the pH was adjusted to 10 by addition of an NH4OH solution. The mixture was extracted with EtOAc (50 mL×3) and the combined extracts dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to afford 8 mg, (20%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((6-fluoro-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl)-N2-methylpyrimidine-2,4-diamine as a white solid. 1H NMR (500 MHz, DMSO) δ 11.8 (brs, 1H), 11.3 (brs, 1H), 9.33 (brs, 1H), 7.85 (d, J=5 Hz, 1H), 7.65 (d, 0.1=10 Hz, 1H), 7.58 (d, J=3 Hz, 1H), 6.51 (s, 1H), 6.00-6.20 (brs, 2H), 5.06 (s, 2H), 3.16 (s, 3H), 1.81 (s, 1H), 0.85 (s, 2H), 0.59 (s, 2H); MS (ESI): m/z=379.3 [M+1]+.

後処理

  1. extractionThe mixture was extracted with EtOAc (50 mL×3)
  2. dry with materialthe combined extracts dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-42b5918875d84f5a93559af08fd8821d
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08815877B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート