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Hydrochloric Acid → 5-(2-benzyl-2H-indazol-6-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1972907
ノート
印刷プレビュー

反応式

HRID 1972907 の反応式
[NH2:1][C:2]1[C:7]2=[C:8]([C:24]3[CH:25]=[CH:26][C:27]4[C:31]([CH:32]=3)=[N:30][N:29]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:28]=4)[CH:9]=[C:10]([C:11]3[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1.Cl>CO.O1CCOCC1>[CH2:33]([N:29]1[CH:28]=[C:27]2[C:31]([CH:32]=[C:24]([C:8]3[CH:9]=[C:10]([C:11]4[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=4)[N:6]4[C:7]=3[C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)[CH:25]=[CH:26]2)=[N:30]1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=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 2

HCID 313Hydrochloric AcidHCID 58529584tert-butyl 4-[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]-3,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 585297595-(2-benzyl-2H-indazol-6-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine収率 112%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

To a solution of tert-butyl 4-[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]-3,6-dihydropyridine-1(2H)-carboxylate (564 mg, 1.08 mmol) in MeOH (4 mL) was added 4M HCl in dioxane (2 mL). The mixture was stirred at rt for 41 h. The mixture was concentrated and the residue was dissolved in 3:1 CHCl3/isopropanol (25 mL). The mixture was washed with saturated, aqueous NaHCO3 (25 mL), brine, dried (Na2SO4) and concentrated to dryness to afford 510 mg (96%) of the desired product, which contained trace impurities. 1H NMR (400 MHz, DMSO-d6) δ 8.54-8.58 (s, 1 H), 7.92 (s, 1 H), 7.80 (d, 1 H), 7.61 (s, 1 H), 7.27-7.37 (m, 5 H), 7.14 (dd, 1 H), 7.01-7.06 (m, 1 H), 6.75 (s, 1 H), 5.65 (s, 2 H), 3.40-3.48 (m, 2 H), 2.92 (t, 1 H), 2.42-2.49 (m, 2 H); ES-MS m/z 422.06 [M+H]+, HPLC RT (min) 1.03 min.

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in 3:1 CHCl3/isopropanol (25 mL)
  3. washThe mixture was washed with saturated, aqueous NaHCO3 (25 mL), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-ff24c677e08a4811bc788ae3bb032efd
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431695B2

反応ノート

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