2-Naphthalenesulfonyl chloride → N-(2-{[(3-Hydroxypropyl)amino]methyl}-3,4-dihydro-2H-chromen-7-yl)naphthalene-2-sulfonamide

HRID 49462

반응식

HRID 49462 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12]O)[O:9]2)=[CH:4][CH:3]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24](Cl)(=[O:26])=[O:25].[NH2:28][CH2:29][CH2:30][CH2:31][OH:32]>N1C=CC=CC=1.O>[OH:32][CH2:31][CH2:30][CH2:29][NH:28][CH2:12][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([NH:1][S:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)(=[O:26])=[O:25])=[CH:3][CH:4]=2)[O:9]1

참가 물질

6

반응물 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 90863-Amino-1-propanolHCID 10511549(7-Aminochroman-2-yl)methanol

생성물 1

HCID 10202719N-(2-{[(3-Hydroxypropyl)amino]methyl}-3,4-dihydro-2H-chromen-7-yl)naphthalene-2-sulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

A solution of (7-amino-3,4-dihydro-2H-chromen-2-yl)methanol (25 mg, 140 μmol) in pyridine is treated with 2-naphthalenesulfonylchloride (70 mg, 308 μmol) at ambient temperature for 1 h, treated with 3-amino-1-propanol (3 mmol, 0.23 mL), heated at 80° C. for 3 h, diluted with water and extracted with ethyl acetate. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue is purified by reverse phase preparative HPLC to give the title product, M+H 427, retention time 7.92 min.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-b252316eb42d4f76a074015cae6cf308
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706757B2

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