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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-[(3-Bromo-2-methylphenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

HRID 564544
ノート
印刷プレビュー

反応式

HRID 564544 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26](O)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].Cl.[Br:35][C:36]1[C:37]([CH3:44])=[C:38]([CH2:42][NH2:43])[CH:39]=[CH:40][CH:41]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:35][C:36]1[C:37]([CH3:44])=[C:38]([CH2:42][NH:43][C:26]([C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:21]([NH:20][CH2:19][C:10]3[C:11]([NH:12][CH:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[C:6]4[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]4=[N:8][C:9]=3[CH2:32][CH3:33])=[O:22])[CH:24]=2)=[O:27])[CH:39]=[CH:40][CH:41]=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 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic AcidHCID 670065313-Bromo-2-methyl-benzylamine hydrochloride

生成物 1

HCID 57813355N-[(3-Bromo-2-methylphenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide
収率 110.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (918 mg, 0.002 mol) and [(3-bromo-2-methylphenyl)methyl]amine hydrochloride (521 mg, 0.0022 mol) in DCM (25 mL) was treated with HATU (912 mg, 0.0024 mol) followed by TEA (0.404 g, 0.56 mL, 0.004 mol). The reaction was stirred overnight at room temperature. LC-MS showed that the reaction was complete. The reaction was quenched with sat. aq. NaHCO3. The aqueous phase was re-extracted with DCM (2×). Combined organic extracts were washed with H2O, then sat. aq. NaCl and dried (Na2SO4), then concentrated to give a residue (1.4 g). This was purified on the ‘CombiFlash’ using 40 g silica gel column [DCM-MeOH, 0-10%]. This afforded the title compound as a glassy, pale yellow foam [1.35 g (Quant.)]. LC-MS m/z 634.7 (M+H)+.

後処理

  1. customThe reaction was quenched with sat. aq. NaHCO3
  2. extractionThe aqueous phase was re-extracted with DCM (2×)
  3. washCombined organic extracts were washed with H2O
  4. dry with materialsat. aq. NaCl and dried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-7f2b8fb2505549e0a349c50b7137673f
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08067408B2

反応ノート

読み込み中…

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