Water → HCID 178464666, compound

HRID 1044683Notes

Reaction equation

HRID 1044683 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-3518fa5e46074047a6814c135b3f9047
Source dataset
uspto-grants-2013_10
Patent number
US08563723B2

Reaction notes

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