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Dimethylamine → 4-(6-Dimethylamino-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 967415
ノート
印刷プレビュー

反応式

HRID 967415 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17](Cl)[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][NH:26][CH3:27]>CO.C(Cl)Cl.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([N:26]([CH3:27])[CH3:25])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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 674DimethylamineHCID 57500931Tert-butyl 4-[(6-chloro-3-nitropyridin-2-yl)amino]piperidine-1-carboxylate

生成物 1

HCID 691571204-(6-Dimethylamino-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester収率 104.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To a stirring solution of 6 g (0.016 mol) of 4-(6-chloro-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester in MeOH/CH2Cl2 (84 mL/15 mL) was added 2.2 g (0.05 mol) of dimethylamine in THF (25 mL). The reaction mixture was stirred at room temperature for 16 h, and was then concentrated. The crude product was then dissolved in CH2Cl2 (400 mL) and washed with saturated NaHCO3 (2×200 mL). The washes were combined and extracted with EtOAc (100 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford 6.1 g (99%) of the desired product as a bright yellow solid. MS (electrospray): exact mass calculated for C17H27N5O4, 365.21; m/z found, 388.19 [M+Na]+. 1H NMR (400 MHz, CDCl3): 8.74 (d, J=7.07 Hz, 1H), 8.18 (d, J=9.4 Hz, 1H), 5.97 (d, J=7.3 Hz, 1H), 4.28-4.16 (m, 1H), 4.07-3.93 (m, 2H), 3.17 (s, 6H), 3.01 (t, J=11.9 Hz, 2H), 2.05 (dd, J=12.4 Hz and 3.03 Hz, 2H), 1.60-1.50 (m, 2H), 1.47 (s, 9H).

後処理

  1. concentrationwas then concentrated
  2. dissolutionThe crude product was then dissolved in CH2Cl2 (400 mL)
  3. washwashed with saturated NaHCO3 (2×200 mL)
  4. extractionextracted with EtOAc (100 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d040f54703ca4a55a8622be3bd143d62
出典データセット
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06953793B2

反応ノート

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