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

Formaldehyde → 6-tert-butyl-8-fluoro-2-(2-hydroxymethyl-3-{1-methyl-5-[5-(6-methyl-2,6-diaza-spiro[3.3]hept-2-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridazin-3-yl}-phenyl)-2H-phthalazin-1-one

HRID 449600
ノート
印刷プレビュー

反応式

HRID 449600 の反応式
[CH2:1]1[C:4]2([CH2:7][NH:6][CH2:5]2)[CH2:3][N:2]1[C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[C:20](=[O:21])[N:19]([CH3:22])[N:18]=[C:17]([C:23]3[C:24]([CH2:45][OH:46])=[C:25]([N:29]4[N:38]=[CH:37][C:36]5[C:31](=[C:32]([F:43])[CH:33]=[C:34]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:35]=5)[C:30]4=[O:44])[CH:26]=[CH:27][CH:28]=3)[CH:16]=2)=[N:12][CH:13]=1.C=O.[C:49]([BH3-])#N.[Na+]>CO>[C:39]([C:34]1[CH:35]=[C:36]2[C:31](=[C:32]([F:43])[CH:33]=1)[C:30](=[O:44])[N:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:17]3[CH:16]=[C:15]([NH:14][C:11]4[CH:10]=[CH:9][C:8]([N:2]5[CH2:3][C:4]6([CH2:7][N:6]([CH3:49])[CH2:5]6)[CH2:1]5)=[CH:13][N:12]=4)[C:20](=[O:21])[N:19]([CH3:22])[N:18]=3)[C:24]=1[CH2:45][OH:46])[N:38]=[CH:37]2)([CH3:40])([CH3:41])[CH3:42]
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

5

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 667419712-(3-(5-(5-(2,6-diazaspiro[3.3]heptan-2-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)-2-(hydroxymethyl)phenyl)-6-tert-butyl-8-fluorophthalazin-1(2H)-one

生成物 1

HCID 566556676-tert-butyl-8-fluoro-2-(2-hydroxymethyl-3-{1-methyl-5-[5-(6-methyl-2,6-diaza-spiro[3.3]hept-2-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridazin-3-yl}-phenyl)-2H-phthalazin-1-one
収率 221.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

In a 25 mL round-bottomed flask, 2-(3-(5-(5-(2,6-diazaspiro[3.3]heptan-2-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)-2-(hydroxymethyl)phenyl)-6-tert-butyl-8-fluorophthalazin-1(2H)-one (146 mg, 234 μmol), 30% formaldehyde (42.2 mg, 38.8 μl, 1.41 mmol) and sodium cyanoborohydride (177 mg, 2.81 mmol) were combined with methanol (9 ml) to give an orange solution. The reaction mixture was stirred at 25° C. for 4 h. The crude reaction mixture was concentrated in vacuo, diluted with 10 mL 0.1 M NaOH and extracted with DCM (3×15 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 10% MeOH in DCM). The light yellow powder was dried under vacuum at 25° C. for 3 hrs to give 0.33 g (22%) of the title compound. (M+H)+=637 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ: 8.37 (s, 1H), 8.28 (d, J=2.3 Hz, 1H), 8.13 (s, 1H), 7.38-7.71 (m, 6H), 6.75-6.93 (m, 2H), 4.40 (s, 2H), 3.96 (s, 4H), 3.88 (s, 3H), 3.47 (s, 4H), 2.37 (s, 3H), 1.42 (s, 9H).

後処理

  1. customto give an orange solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additiondiluted with 10 mL 0.1 M NaOH
  5. extractionextracted with DCM (3×15 mL)
  6. dry with materialThe organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 40 g, 0% to 10% MeOH in DCM)
  9. customThe light yellow powder was dried under vacuum at 25° C. for 3 hrs

出典と根拠

ORDレコード
ord-7e448edbadc64b518cb77b16e5d33ae6
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481540B2

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