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

Trifluoromethanesulfonic acid → 1-(5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-(3-fluorophenyl)urea

HRID 1621678
ノート
印刷プレビュー

反応式

HRID 1621678 の反応式
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:22][C:23]4[CH:24]=[CH:25][C:26]([NH:29][C:30]([NH:32][C:33]5[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=5)=[O:31])=[N:27][CH:28]=4)=[N:18][CH:19]=[CH:20][CH:21]=3)[N:10]=2)=CC=1.FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]2[C:17]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([NH:29][C:30]([NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=4)=[O:31])=[N:27][CH:28]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)[N:10]=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 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 666117991-(5-(3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-(3-fluorophenyl)urea

生成物 1

HCID 595482001-(5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-(3-fluorophenyl)urea収率 58%

試薬・触媒・溶媒 1

HCID 6422
Trifluoroacetic acid
溶媒

実験手順

A solution of 1-(5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-(3-fluorophenyl)urea (0.0824 g, 0.123 mmol) and trifluoromethanesulfonic acid (TCI) (0.02 mL, 0.225 mmol) in TFA (1 mL) was stirred at rt for 3 h, 50° C. for 3 h, then 75° C. for overnight. Saturated sodium bicarbonate was added slowly to quench the reaction and the resulting precipitate was collected by filtration. The crude product was purified by preparative HPLC using Phenomenex, Gemni NX 5 micron C18 150×30 mm column (10%-90% CH3CN w/0.1% TFA/H2O w/0.1% TFA in 10 min). The resulting fraction was concentrated to dryness in vacuo. Saturated sodium bicarbonate was added to the residue and the resulting yellow precipitate was collected by filtration, washed with water, and dried in a vacuum oven to give 1-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-(3-fluorophenyl)urea (0.0305 g, 58% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.89 (s, 1H); 10.49 (br. s., 1H); 9.38 (s, 1H); 8.71-8.83 (m, 2H); 8.29-8.39 (m, 1H); 8.23 (dd, J=9.00, 2.35 Hz, 1H); 7.87 (br. s., 1H); 7.74 (br. s., 1H); 7.47-7.65 (m, 2H); 7.34 (q, J=7.89 Hz, 1H); 7.20 (d, J=8.02 Hz, 1H); 6.92 (dd, J=7.63, 4.69 Hz, 1H); 6.76-6.87 (m, 1H); 2.44 (s, 3H). m/z (ESI, +ve ion) 432.0 (M+H)+.

後処理

  1. customto quench
  2. customthe reaction
  3. filtrationthe resulting precipitate was collected by filtration
  4. customThe crude product was purified by preparative HPLC
  5. customC18 150×30 mm column (10%-90% CH3CN w/0.1% TFA/H2O w/0.1% TFA in 10 min)
  6. concentrationThe resulting fraction was concentrated to dryness in vacuo
  7. additionSaturated sodium bicarbonate was added to the residue
  8. filtrationthe resulting yellow precipitate was collected by filtration
  9. washwashed with water
  10. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-68b5826f616d41ee8cec85fa09d8f8a3
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772480B2

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