1H-Indole-5-sulfonamide → HCID 178464642、化合物

HRID 1484465

反応式

HRID 1484465 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 178464642HCID 178464642、化合物収率 87%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8a2f8b2419a246669fe99ede3e634c33
出典データセット
uspto-grants-2016_08
特許番号
US09422244B2

関連ノート

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