1H-Indole-5-sulfonamide → HCID 178464642, 화합물

HRID 1484465

반응식

HRID 1484465 반응식
CS[C:3]([N:7]1[N:11]=[CH:10][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:8]1)=[N:4][CH2:5][CH3:6].[NH:16]1[C:24]2[C:19](=[CH:20][C:21]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:22][CH:23]=2)[CH:18]=[CH:17]1>C(#N)C>[CH2:8]1[C:9]2([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:10]=[N:11][N:7]1[C:3]([NH:4][CH2:5][CH3:6])=[N:28][S:25]([C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[NH:16][CH:17]=[CH:18]2)(=[O:27])=[O:26]

참가 물질

4

반응물 2

HCID 216831001H-Indole-5-sulfonamideHCID 53354231N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboximidothioic acid methyl ester

생성물 1

HCID 178464642HCID 178464642, 화합물수율 87%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

100 mg (1 mol equiv.) N-Ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboximidothioic acid methyl ester and 92.5 mg (1.05 mol equiv.) 1H-indole-5-sulfonic acid amide were added to 3 mL acetonitrile. The reaction mixture was refluxed overnight and volatiles were removed under reduced pressure. The residue was taken up in ethyl acetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (Et2O:EtOAc=1:1) afforded 152 mg (87%) 1H-indole-5-sulfonic acid (2,3-diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methyleneamide. 1H NMR (400 MHz, CDCl3) δ 1.14 (t, J=7.2 Hz, 3H), 1.59-1.79 (m, 8H), 3.43-3.51 (m, 2H), 3.79 (br.s., 2H), 6.63-6.65 (m, 1H), 6.76 (s, 1H), 6.99 (br.s., 1H), 7.30 (t, J=2.8 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 7.76 (dd, J=8.6, 1.8 Hz, 1H), 8.27 (br.s., 1H), 8.54 (br.s., 1H).

후처리

  1. temperatureThe reaction mixture was refluxed overnight
  2. customvolatiles were removed under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography on silica gel (Et2O:EtOAc=1:1)

출처 및 근거

ORD 기록
ord-8a2f8b2419a246669fe99ede3e634c33
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422244B2

연결된 노트

불러오는 중…