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Diisopropylethylamine → 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide

HRID 468673
ノート
印刷プレビュー

反応式

HRID 468673 の反応式
[CH3:1][C:2]1([CH3:26])[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])(=[O:10])=[O:9])[CH2:5][C:4]2[CH:20]=[C:21]([C:23]([OH:25])=O)[S:22][C:3]1=2.CCN(C(C)C)C(C)C.[O:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]1[O:42][NH2:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH3:1][C:2]1([CH3:26])[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])(=[O:9])=[O:10])[CH2:5][C:4]2[CH:20]=[C:21]([C:23]([NH:43][O:42][CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][O:36]3)=[O:25])[S:22][C:3]1=2
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 4

HCID 81531DiisopropylethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669317517,7-Dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid

生成物 1

HCID 86651322
7,7-dimethyl-5-(2-nitrophenylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide
収率 94.8%

反応条件

温度
0 °C

実験手順

A solution of 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid (20 g, 50 mmol) was cooled to 0° C. DIPEA (32.3 g, 250 mmol) was added and the solution was stirred at 0° C. for 30 minutes. O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (5.8 g, 50 mmol) and HATU (22.8 g, 60 mmol) were then added and the reaction was allowed to warm to room temperature overnight. The reaction mixture was washed with water, brine and dried over anhydrous Na2SO4, concentrated and purified by silica gel chromatography (20-50% EtOAc/hexane) to afford product (23.5 g, 94%). LCMS (FA) ES+ 496; 1H NMR (400 MHz, DMSO) δ 11.60 (s, 1H), 8.10 (dd, J=7.7, 1.5 Hz, 1H), 8.02 (dd, J=7.7, 1.5 Hz, 1H), 7.90 (dtd, J=17.6, 7.5, 1.4 Hz, 2H), 7.41 (s, 1H), 4.92 (s, 1H), 4.33 (s, 2H), 4.00 (s, 1H), 3.50 (d, J=11.1 Hz, 1H), 3.38 (s, 2H), 1.72 (d, J=22.2 Hz, 3H), 1.53 (s, 3H), 1.27 (s, 6H).

後処理

  1. temperatureto warm to room temperature overnight
  2. washThe reaction mixture was washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (20-50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-3d056f52b12d46cf9df97633a4bb7488
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08624040B2

反応ノート

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