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

HRID 1812088
ノート
印刷プレビュー

反応式

HRID 1812088 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]=[CH:35][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:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:31])=[N:27][CH:28]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)[N:10]=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

5

反応物 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 666119881-(5-(3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-phenylurea

生成物 1

HCID 595482161-(5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-phenylurea収率 47%

試薬・触媒・溶媒 1

HCID 6422
Trifluoroacetic acid
溶媒

反応条件

温度
50 °C

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-phenylurea (0.0707 g, 0.108 mmol) and trifluoromethanesulfonic acid (TCI) (0.02 mL, 0.225 mmol) in 1 mL of TFA was stirred at rt for 3 h then heated to 50° C. and stirred for 3 h. Then the mixture was heated at 75° C. 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-phenylurea (0.0210 g, 47% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.87 (s, 1H); 10.28 (br. s., 1H); 9.30 (s, 1H); 8.71-8.84 (m, 2H); 8.34 (dd, J=4.60, 1.86 Hz, 8.22 (dd, J=9.00, 2.74 Hz, 1H); 7.87 (br. s., 1H); 7.74 (br. s., 1H); 7.47-7.58 (m, 3H); 7.31 (t, J=7.92 Hz, 2H); 7.01 (t, J=7.43 Hz, 1H); 6.92 (dd, J=7.83, 4.69 Hz, 1H); 2.44 (s, 3H). m/z (ESI, +ve ion) 414.0 (M+H)+.

後処理

  1. temperatureThen the mixture was heated at 75° C. overnight
  2. customto quench
  3. customthe reaction
  4. filtrationthe resulting precipitate was collected by filtration
  5. customThe crude product was purified by preparative HPLC
  6. customC18 150×30 mm column (10%-90% CH3CN w/0.1% TFA/H2O w/0.1% TFA in 10 min)
  7. concentrationThe resulting fraction was concentrated to dryness in vacuo
  8. additionSaturated sodium bicarbonate was added to the residue
  9. filtrationthe resulting yellow precipitate was collected by filtration
  10. washwashed with water
  11. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-6bf54197cf8f4c89ba61e521625cd762
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362241B2

反応ノート

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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