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

HRID 1812360

반응식

HRID 1812360 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 71481004N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide수율 79.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

The two batches of N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide (total 0.47 g, 1.0 mmol) were placed in two 150 mL round-bottomed flasks. To each flask were added 1 N hydrochloric acid (0.6 mL each, total 1.2 mL) and 3 mL THF (3 mL each, total 6 mL). After stirring at room temperature for 10 min, the two reaction mixtures were combined and most of THF was removed in vacuo, and the residue was partitioned between saturated aqueous ammonium chloride (30 mL) and 25% isopropanol in chloroform (30 mL). The aqueous phase was extracted with 25% isopropanol in chloroform (2×20 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (25 g, eluent: iPrOH in CHCl3 0% to 10%) to afford N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide (0.233 g, 77% yield) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.64 (d, J=2.74 Hz, 1H) 7.30 (d, J=2.74 Hz, 1H) 6.68 (br. s., 1H) 3.83 (br. s., 2H) 3.66-3.71 (m, 4H) 3.22-3.27 (m, 4H). m/z (ESI, positive ion): 293.0 (M+H)+.

후처리

  1. customthe two reaction mixtures
  2. customwas removed in vacuo
  3. customthe residue was partitioned between saturated aqueous ammonium chloride (30 mL) and 25% isopropanol in chloroform (30 mL)
  4. extractionThe aqueous phase was extracted with 25% isopropanol in chloroform (2×20 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography (25 g, eluent: iPrOH in CHCl3 0% to 10%)

출처 및 근거

ORD 기록
ord-f175e30932634e3d84351e1c31f2875f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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