Hydroxylamine → n-(4-(1,2,4-Oxadiazol-3-yl)benzyl)-n-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

HRID 1011550노트

반응식

HRID 1011550 반응식
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([CH:19]2[CH2:24][CH:23]3[CH:25]([OH:26])[CH:20]2[CH2:21][CH2:22]3)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[NH2:29]O.C([O:34][CH2:35]C)(=O)C>C(O)C.C(OC(OCC)OCC)C>[O:34]1[CH:35]=[N:29][C:1]([C:3]2[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH:19]3[CH2:24][CH:23]4[CH:25]([OH:26])[CH:20]3[CH2:21][CH2:22]4)[S:9]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)(=[O:11])=[O:10])=[CH:27][CH:28]=2)=[N:2]1

참가 물질

6

반응물 3

HCID 787HydroxylamineHCID 8857Ethyl AcetateHCID 59497811N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

생성물 1

HCID 59497796n-(4-(1,2,4-Oxadiazol-3-yl)benzyl)-n-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide수율 44%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 31214Ethyl orthoformate용매

실험 절차

A mixture of N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (380 mg, 0.91 mmol) and hydroxylamine (500 up was refluxed in 20 mL ethanol for 2 h. The reaction was concentrated and dried under high vacuum. A portion of the crude amide oxime (25 mg) which was obtained was refluxed in triethylorthoformate (2 mL) for 5 h. The reaction was diluted into 20 mL ethyl acetate, washed with brine, and purified by flash chromatography on 4 g silica gel with 0 to 30% ethyl acetate in hexane to yield N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (11 mg, 44%). 1H NMR (400 MHz, CDCl3) δ ppm 8.73 (1H, s), 8.00-8.08 (2H, m), 7.68-7.79 (2H, m), 7.40-7.49 (4H, m), 4.83 (2H, q, J=17.54 Hz), 4.02-4.11 (1H, m), 3.83 (1H, s), 1.88 (1H, br. s.), 1.58-1.68 (2H, m), 1.43-1.55 (3H, m), 1.06-1.16 (2H, m). LC/MS R.T.=2.35 min; [M+H]+=460.13.

후처리

  1. concentrationThe reaction was concentrated
  2. customdried under high vacuum
  3. customA portion of the crude amide oxime (25 mg) which was obtained
  4. washwashed with brine
  5. custompurified by flash chromatography on 4 g silica gel with 0 to 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-e0090dc6e1af461d8c69d440d7a7ef16
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977362B2

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