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

HRID 2273981Notes

Reaction equation

HRID 2273981 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-cb463a8a6cbd4499b08613c9bdab724e
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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