1,2-Dichloroethane → HCID 59715911, compound

HRID 2223717Notes

Reaction equation

HRID 2223717 reaction equation
Cl.[CH3:2][CH:3]([CH3:23])[C@H:4]([NH:8][C:9]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([CH3:22])[CH:13]=1)=[O:10])[C:5]([OH:7])=O.[CH2:24]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH2:24]([CH:31]1[CH2:36][CH2:35][N:34]([C:5]([C@@H:4]([NH:8][C:9]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([CH3:22])[CH:13]=2)=[O:10])[CH:3]([CH3:2])[CH3:23])=[O:7])[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 317384-BenzylpiperidineHCID 757711-HydroxybenzotriazoleHCID 69219960HCID 69219960, compound

Product 1

HCID 59715911HCID 59715911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-3-methyl-2-[3-(2-methyl-quinolin-4-yl)-ureido]-butyric acid hydrochloride (337.8 mg, 1 mmol), 4-benzylpiperidine (175.3 mg, 1 mmol), HOBt (183 mg, 1.2 mmol) and TEA (0.35 mL, 2.5 mmol) in DMF (10 mL) is added EDC (230.0 mg, 1.2 mmol). The mixture is stirred for 15 h at room temperature and then quenched with sat. aqueous Na2CO3 (30 mL). The aqueous phase is extracted with CH2Cl2 (3×20 mL). The combined extracts are dried (Na2SO4), filtered and evaporated. The residue is purified by flash chromatography (SiO2, CH2Cl2/MeOH, 5/1) to provide the title compound.

Workup

  1. customquenched with sat. aqueous Na2CO3 (30 mL)
  2. extractionThe aqueous phase is extracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by flash chromatography (SiO2, CH2Cl2/MeOH, 5/1)

Sources & evidence

ORD record
ord-96690bdae62e4e4a98913a08c4f954c3
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

Loading…