1,2-Dichloroethane → HCID 91249054, compound

HRID 1786016Notes

Reaction equation

HRID 1786016 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:35]=[CH:34][C:9]([C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]([N:22]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:23](=[O:25])[CH3:24])[CH2:14][C@@H:13]2[CH3:33])=[O:11])=[CH:8][CH:7]=1.[CH3:36][N:37]1[CH2:44][CH2:43][CH2:42][C@H:38]1[C:39](O)=[O:40].C(Cl)CCl>C(Cl)Cl.N1C=CC=CC=1>[C:23]([N:22]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C@H:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]([C:10]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:39]([C@@H:38]3[CH2:42][CH2:43][CH2:44][N:37]3[CH3:36])=[O:40])=[CH:35][CH:34]=2)=[O:11])[CH:13]([CH3:33])[CH2:14]1)(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 643474N-Methyl-L-prolineHCID 58859953HCID 58859953, compound

Product 1

HCID 91249054HCID 91249054, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-N-{1-[4-(3-Amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (100 mg, 0.204 mmol) was dissolved in methylene chloride (2 mL) and pyridine (2 mL). N-methyl proline (33 mg, 0.255 mmol) and EDC (63 mg, 0.255 mmol) were added and the reaction was stirred for 1 hour. The mixture was partitioned between methylene chloride and water; the methylene chloride layer was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (ethyl acetate) to afford the product.

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. dry with materialthe methylene chloride layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography (ethyl acetate)
  6. customto afford the product

Sources & evidence

ORD record
ord-8e80d6b8a1c748f68ed40bad6c5176e6
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…