Diisopropylethylamine → HCID 178464648, compound

HRID 2273980Notes

Reaction equation

HRID 2273980 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].CCN(C(C)C)C(C)C.[CH2:22]([NH:24][C:25]([N:27]1[N:31]=[CH:30][C:29]2([CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:28]1)=[NH:26])[CH3:23]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:26]=[C:25]([N:27]2[N:31]=[CH:30][C:29]3([CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:28]2)[NH:24][CH2:22][CH3:23])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 178464598HCID 178464598, compound

Product 1

HCID 178464648HCID 178464648, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.50 g 3-cyanobenzenesulfonyl chloride 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 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 3.54 g (57%) of a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.17 (t, J=8 Hz, 3H), 1.65-1.86 (m, 8H), 3.41-3.50 (m, 2H), 3.87 (br.s., 2H), 6.70-6.80 (br.s., 1H), 6.87 (s, 1H), 7.60 (t, J=8 Hz, 1H), 7.77 (d, J=8 Hz, 1H), 8.17 (d, J=8 Hz, 1H), 8.23 (br.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-7bad2d9f36954c1f8925c6387701812a
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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