Diisopropylethylamine → 3-{[(2,3-Diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]-sulfamoyl}-benzoic acid methyl ester

HRID 1044711

반응식

HRID 1044711 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:5]=1.CCN(C(C)C)C(C)C.[CH2:24]([NH:26][C:27]([N:29]1[N:33]=[CH:32][C:31]2([CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:30]1)=[NH:28])[CH3:25]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10](=[O:12])(=[O:11])[N:28]=[C:27]([N:29]2[N:33]=[CH:32][C:31]3([CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:30]2)[NH:26][CH2:24][CH3:25])[CH:5]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl esterHCID 178464598HCID 178464598, 화합물

생성물 1

HCID 1784646503-{[(2,3-Diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]-sulfamoyl}-benzoic acid methyl ester수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4.07 g 3-chlorosulfonyl-benzoic acid methyl ester in 150 mL DCM were added 17.69 mL (6.0 equiv.) DiPEA and 4.00 g (1.0 equiv.) N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboxamidine. The reaction mixture was stirred overnight at room temperature under N2 atmosphere, and extracted with water. The organic phase was dried over Na2SO4 and evaporated, and the residue was purified by automated flash chromatography (EtOAc/PA 1:1) to give 4.80 g (71%) of a yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=8 Hz, 3H), 1.62-1.86 (m, 8H), 3.42-3.53 (m, 2H), 3.87 (s, 2H), 3.95 (s, 3H), 6.83 (s, 1H), 6.83-6.95 (broad peak, 1H), 7.56 (t, J=8 Hz, 1H), 8.13-8.18 (m, 2H), 8.61 (s, 1H).

후처리

  1. extractionextracted with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. customthe residue was purified by automated flash chromatography (EtOAc/PA 1:1)

출처 및 근거

ORD 기록
ord-54d396e0d79e4cb5910ed097cc451ebb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563723B2

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