HCID 86647061、化合物 → N-(5-amino-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide

HRID 1621785

反応式

HRID 1621785 の反応式
[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([N:19]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1>C1COCC1.Cl>[NH2:19][C:5]1[CH:6]=[C:7]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)(=[O:10])=[O:11])[C:2]([Cl:1])=[N:3][CH:4]=1

参加物

4

反応物 1

HCID 86647061HCID 86647061、化合物

生成物 1

HCID 71480919N-(5-amino-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide収率 80.2%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.520 g, 1.116 mmol) in THF (8 mL) and hydrochloric acid, 2N (J. T. Baker) (0.837 mL, 1.674 mmol) was stirred at rt in a sealed tube for 30 min. The reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (80 g, 20% to 40% acetone in hexanes) to give the product as a yellow solid (0.270 g). m/z (ESI, +ve ion) 302.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.80 (dd, J=8.77, 4.97 Hz, 2H); 7.61 (d, J=2.63 Hz, 1H); 7.34 (d, J=2.48 Hz, 1H); 7.16 (t, J=8.48 Hz, 2H); 6.82 (br. s., 1H); 3.84 (br. s., 2H).

後処理

  1. customThe reaction mixture was partitioned between EtOAc and sat. NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (80 g, 20% to 40% acetone in hexanes)

出典と根拠

ORDレコード
ord-df1b4696192842299d235ec8c83c52ce
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

関連ノート

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