Water → HCID 178464666, compound

HRID 1396040Notes

Reaction equation

HRID 1396040 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]([N:15]2[N:19]=[CH:18][C:17]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:16]2)SC)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:24].[CH2:25]([NH2:27])[CH3:26].O>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]([N:15]2[N:19]=[CH:18][C:17]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:16]2)[NH:27][CH2:25][CH3:26])(=[O:10])=[O:9])=[CH:4][C:3]=1[F:24]

Participants

5

Reactant 3

HCID 962WaterHCID 6341EthylamineHCID 66933446HCID 66933446, compound

Product 1

HCID 178464666HCID 178464666, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 840 mg 4-amino-N-[(2,3-diaza-spiro[4.4]non-3-en-2-yl)-methylsulfanyl-methylene]-3-fluoro-benzenesulfonamide (crude) in 25 mL MeOH was added 3.43 mL of a 70% aqueous solution of ethylamine. The mixture was stirred for 1 h. at room temperature, water was added, and the mixture was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography (EA/PA 3:1) to give 260 mg (33% over 2 steps) of 4-amino-N-[(2,3-diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]-3-fluoro-benzenesulfonamide as a brown oil. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=7.2 Hz, 3H), 1.57-1.87 (m, 7H), 3.43-3.53 (m, 2H), 3.82 (s, 2H), 4.02-4.07 (m, 2H), 6.77 (t, J=8.4 Hz, 1H), 6.80 (s, 1H), 7.50-7.58 (m, 2H) [NH2 invisible].

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (EA/PA 3:1)

Sources & evidence

ORD record
ord-adccefc59fbf40d2847bb2adb55404e4
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

Loading…