Pyridine → 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide

HRID 2235131노트

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HRID 2235131 반응식
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:6]=1)=[NH:4].N1C=CC=CC=1.C(C(CCCC)[CH2:44][O:45]C(Cl)=O)C>CN(C)C=O>[O:45]=[C:44]1[O:1][N:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]3[CH:22]=[C:21]4[C:17]([CH2:18][CH2:19][N:20]4[S:23]([C:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=4[O:33][CH3:34])(=[O:25])=[O:24])=[CH:16][CH:15]=3)=[O:13])=[CH:7][CH:6]=2)[NH:4]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 178490720HCID 178490720, 화합물

생성물 1

HCID 1354020001-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A solution of 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(N-hydroxycarbamimidoyl)-phenyl]-amide (254 mg, 0.51 mmol) in dimethylformamide (3.5 ml) was treated with pyridine (0.04 ml, 1 equiv.) and the mixture was cooled to 0° C. Chloroformic acid 2-ethylhexyl ester (98 mg, 0.51 mmol, 1 equiv.) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min, then quenched with water. The slurry was extracted three times with ethyl acetate. The combined organic layers were dried with Na2SO4 and the solvent was evaporated. The crude compound was suspended in xylene and heated at reflux for 2 hours. After cooling to room temperature, the solid was filtered and dried under high vacuum, yielding 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide as a white solid, 114 mg (43%). MS (ISP): m/e=525.2 (M−H), δH (300 MHz; d6-DMSO) 10.31 (1H, s), 7.55-7.80 (8H, m), 7.28 (1H, d), 7.16 (1H, d), 4.04 (2H, t), 3.60 (3H, s), 3.06 (2H, t).

후처리

  1. customquenched with water
  2. extractionThe slurry was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. customthe solvent was evaporated
  5. temperatureheated
  6. temperatureat reflux for 2 hours
  7. temperatureAfter cooling to room temperature
  8. filtrationthe solid was filtered
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-0d58be7e9b8943349f9393fa0662e726
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713996B2

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