Triethylamine → 2-Chlorobenzenesulfonic acid 3-[[1-(aminoiminomethyl)piperidin-4-yl]methoxy]phenyl ester

HRID 482083노트

반응식

HRID 482083 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([O:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[NH2:33][N:34]=[CH:35]S(O)(=O)=O>CN(C=O)C>[NH2:33][N:34]=[CH:35][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([O:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])(=[O:17])=[O:18])[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 542506032-Chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]phenyl ester

생성물 1

HCID 867530142-Chlorobenzenesulfonic acid 3-[[1-(aminoiminomethyl)piperidin-4-yl]methoxy]phenyl ester수율 49.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]phenyl ester (191 mg, 0.5 mmol), as prepared in the preceding step, in DMF (10 mL) containing triethylamine (0.2 mL) and aminoiminomethanesulfonic acid (124 mg, 1.0 mmol) was stirred at room temperature overnight. The DMF was concentrated 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 (105 mg, 49%). 1H-NMR (300 MHz, CDCl3 /DMSO)-d6) δ 1.38 (m, 2H), 1.88 (d, 2H), 2.08 (m, 1H), 3.00 (t, 2H), 3.79 (d, 2H), 4.05 (dd, 2H), 6.61 (dd, 1H) 6.77 (t, 1H), 6.79 (dd, 1H), 7.20 (t, 1H), 7.37 (bs, 3H), 7.50 (m, 1H), 7.92 (d, 2H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C19H22 N3O4SCl: 424.1(M+H), 446.1 (M+Na), Found: 424.3, 446.6

후처리

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

출처 및 근거

ORD 기록
ord-1a53372764f94659aafa9ca611313385
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792769

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