Benzenesulfonyl chloride → N-[2-({[(1R)-1-Phenylethyl]amino}methyl)-3,4-dihydro-2H-chromen-7-yl]-2,1,3-benzoxadiazole-4-sulfonamide

HRID 49463

반응식

HRID 49463 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.[N:14]1[O:15][N:16]=[C:17]2[C:22]([S:23](Cl)(=[O:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:18]=12.C1(S(Cl)(=O)=O)C=CC=CC=1.[C:37]1([C@H:43]([NH2:45])[CH3:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>N1C=CC=CC=1.O>[C:37]1([C@H:43]([NH:45][CH2:12][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:2]([NH:1][S:23]([C:22]4[C:17]5[C:18](=[N:14][O:15][N:16]=5)[CH:19]=[CH:20][CH:21]=4)(=[O:25])=[O:24])=[CH:3][CH:4]=3)[O:9]2)[CH3:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

7

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 6431891-Phenethylamine, (+)-HCID 27354462,1,3-Benzoxadiazole-4-sulfonyl chlorideHCID 10511549(7-Aminochroman-2-yl)methanol

생성물 1

HCID 69884972N-[2-({[(1R)-1-Phenylethyl]amino}methyl)-3,4-dihydro-2H-chromen-7-yl]-2,1,3-benzoxadiazole-4-sulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

A solution of (7-amino-3,4-dihydro-2H-chromen-2-yl)methanol (28.6 mg, 160 μmol) in pyridine is treated with 2,1,3-benzoxadiazole-4-sulfonyl chloride (39 mg, 180 μmol) at ambient temperatures, stirred for 1 h, treated with phenylsulfonyl chloride (23 μL, 180 μmol) stirred for an additional hour at ambient temperatures, treated with (1R)-1-phenyl-1-ethanamine (1.6 mmol, 206 μL), heated to 100° C. for 2 h, cooled to room temperature, 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 465, retention time 3.89 min.

후처리

  1. stirringstirred for an additional hour at ambient temperatures
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue is purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-4be1e33e70914c3a85aad06d6d29f8d9
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706757B2

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