Sodium Hydroxide → 4-(5-(2-Aminopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine 2,2,2-trifluoroacetate

HRID 1621818ノート

反応式

HRID 1621818 の反応式
[NH2:1][C:2]([C:5]1[CH:6]=[C:7]([C:20]2[N:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27](CC3C=CC([O:44][CH3:45])=CC=3)CC3C=CC(OC)=CC=3)[N:21]=2)[C:8]([NH:11][C:12]2[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[N:9][CH:10]=1)([CH3:4])[CH3:3].OS([C:50]([F:53])([F:52])[F:51])(=O)=O.[OH-:54].[Na+]>C(O)(C(F)(F)F)=O>[F:51][C:50]([F:53])([F:52])[C:45]([OH:44])=[O:54].[NH2:1][C:2]([C:5]1[CH:6]=[C:7]([C:20]2[N:25]=[C:24]([CH3:26])[N:23]=[C:22]([NH2:27])[N:21]=2)[C:8]([NH:11][C:12]2[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[N:9][CH:10]=1)([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 66610862HCID 66610862、化合物

生成物 1

HCID 666110444-(5-(2-Aminopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine 2,2,2-trifluoroacetate収率 45.5%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
80 °C

実験手順

A solution of 4-(5-(2-aminopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.025 g, 0.041 mmol) in TFA (1 mL) was treated with triflic acid (0.029 mL, 0.330 mmol), sealed, and heated at 80° C. for 2 h. The reaction was cooled and treated with ice and 10N NaOH until basic. The reaction was partitioned between water and DCM. The aqueous layer was extracted with DCM (3×) and the combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. This material was dissolved in DMSO and purified by prep HPLC (5-50% MeCN/H2O with 0.1% TFA). Product-containing fractions were concentrated in vacuo to give 4-(5-(2-aminopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine 2,2,2-trifluoroacetate (9 mg, 0.019 mmol, 45.5% yield) as an orange solid. m/z (ESI, +ve ion) 367 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.76 (s, 1H); 8.93 (d, J=2.7 Hz, 1H); 8.54 (d, J=2.5 Hz, 1H); 8.50 (d, J=2.7 Hz, 1H); 8.37 (br. s., 3H); 8.13 (dd, J=8.8, 2.7 Hz, 1H); 7.90 (br. s., 1H); 7.80 (br. s., 1H); 6.84 (d, J=9.0 Hz, 1H); 3.85 (s, 3H); 2.45 (s, 3H); 1.68 (s, 6H).

後処理

  1. customsealed
  2. temperatureThe reaction was cooled
  3. customThe reaction was partitioned between water and DCM
  4. extractionThe aqueous layer was extracted with DCM (3×)
  5. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThis material was dissolved in DMSO
  9. custompurified by prep HPLC (5-50% MeCN/H2O with 0.1% TFA)
  10. concentrationProduct-containing fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-3220c4dfa2f544b78bf98f200a33c44a
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

反応ノート

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