Hydrochloric Acid → N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide

HRID 1622009

反応式

HRID 1622009 の反応式
[Cl:1][C:2]1[C:7]([NH:8][S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:6][C:5]([N:18]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1.Cl>C1COCC1>[NH2:18][C:5]1[CH:6]=[C:7]([NH:8][S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[C:2]([Cl:1])=[N:3][CH:4]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86647078N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide

生成物 1

HCID 71481004N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide (0.150 g, 0.328 mmol) in THF (3 mL) was added hydrochloric acid, 2n (JT Baker) (0.020 mL, 0.657 mmol). The reaction was stirred at rt in closed system for 20 min. The reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (24 g, 3% MeOH in DCM) to afford the desired product as a white foam-like solid (70.0 mg). MS (ESI pos. ion) m/z: 293.0. 1H NMR (300 MHz, CDCl3) δ ppm 3.16-3.32 (m, 4H) 3.61-3.74 (m, 4H) 3.84 (br. s., 2H) 6.67 (br. s., 1H) 7.31 (d, J=2.34 Hz, 1H) 7.64 (d, J=2.19 Hz, 1H).

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 layer were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (24 g, 3% MeOH in DCM)

出典と根拠

ORDレコード
ord-2b430f7d7a684989844d90bb0b2c816a
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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