Hydrochloric Acid → HCID 178464668, compound

HRID 1044713Notes

Reaction equation

HRID 1044713 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[N:10]=[CH:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:7]1)=[NH:5])[CH3:2].CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH3:33][C:34]1[CH:35]=[C:36]([S:47](Cl)(=[O:49])=[O:48])[CH:37]=[CH:38][C:39]=1[NH:40][C:41](=[O:46])[C:42]([F:45])([F:44])[F:43].Cl>CN(C=O)C>[CH2:7]1[C:8]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:9]=[N:10][N:6]1[C:4](=[N:5][S:47]([C:36]1[CH:37]=[CH:38][C:39]([NH:40][C:41](=[O:46])[C:42]([F:43])([F:44])[F:45])=[C:34]([CH3:33])[CH:35]=1)(=[O:49])=[O:48])[NH:3][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 536276703-Methyl-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chlorideHCID 178464598HCID 178464598, compound

Product 1

HCID 178464668HCID 178464668, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.23 g N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboxamidine in 5 mL dry DMF was added 0.87 mL (3.0 equiv.) BEMP and the light brown mixture was stirred for 10 minutes at room temperature. Subsequently, 0.33 g (1.1 equiv.) 3-methyl-4-(2,2,2-trifluoro-acetylamino)-benzenesulfonyl chloride was added in one portion and the resulting bright yellow solution was stirred overnight at room temperature. The mixture was cooled in an ice bath, acidified with 1 N HCl, and then extracted three times with EtOAc/Et2O 1:1. The combined organic layers were washed once with water, then with brine, dried over Na2SO4 and evaporated onto silica. Purification with flash chromatography (EtOAc/PA 4:6→5:5) yielded 0.18 g (39%) of a white solid. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=7.2 Hz, 3H), 1.63-1.86 (m, 8H), 2.33 (s, 3H), 3.43-3.52 (m, 2H), 3.83 (s, 2H), 6.77-6.85 (br.s., 1H), 6.83 (s, 1H), 7.73-7.79 (m, 2H), 7.86 (d, J=8.3 Hz, 1H), 8.10 (br.s., 1H).

Workup

  1. stirringthe resulting bright yellow solution was stirred overnight at room temperature
  2. temperatureThe mixture was cooled in an ice bath
  3. extractionextracted three times with EtOAc/Et2O 1:1
  4. washThe combined organic layers were washed once with water
  5. dry with materialwith brine, dried over Na2SO4
  6. customevaporated onto silica
  7. customPurification with flash chromatography (EtOAc/PA 4:6→5:5)

Sources & evidence

ORD record
ord-ed95af783366463f887aa33348e5420a
Source dataset
uspto-grants-2013_10
Patent number
US08563723B2

Reaction notes

Loading…