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

HRID 1484465Notes

Reaction equation

HRID 1484465 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 178464642HCID 178464642, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8a2f8b2419a246669fe99ede3e634c33
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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