Diisopropylethylamine → 2-Chlorobenzenesulfonic acid, 3-[[1-(aminoiminomethyl)piperidin-4-yl]methoxy]-5-methylphenyl ester

HRID 482089Notes

Reaction equation

HRID 482089 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([O:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[NH2:36][N:37]=[CH:38]S(O)(=O)=O>CN(C=O)C>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([O:16][C:11]1[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([O:8][CH2:7][CH:4]2[CH2:5][CH2:6][N:1]([CH:38]=[N:37][NH2:36])[CH2:2][CH2:3]2)[CH:10]=1)(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 158950942-Chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]-5-methylphenyl ester

Product 1

HCID 867530162-Chlorobenzenesulfonic acid, 3-[[1-(aminoiminomethyl)piperidin-4-yl]methoxy]-5-methylphenyl esterYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]-5-methylphenyl ester (396 mg, 1.0 mmol), as prepared in the preceding step, in DMF (10 mL), N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) was stirred at room temperature overnight. The DMF was removed in vacuo and the residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3) to give the title compound as a white foam (159 mg, 36%). 1H-NMR (300 MHz, CDCl3) δ 1.45 (m, 2H), 1.92 (m, 3H), 2.21 (s, 3H), 3.07 (t, 2H), 3.69 (d, 2H), 4.09 (d, 2H), 6.46 (d, 1H), 6.49 (s, 1H), 6.56 (s, 1H), 7.28 (s, 3H), 7.39 (t, 1H), 7.62 (m, 2H), 7.95 (dd, IH). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C20H24N3O4SCl: 438.1 (M+H), 460.1 (M+Na), Found: 438.3, 460.1.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3)

Sources & evidence

ORD record
ord-c1258fa163e84bb1a122fda1378bf00e
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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