Ethyl chloroacetate → N-[(3S)-1-[6-chloro-5-[[(cyclohexylmethyl)amino]carbonyl]-2-quinolinyl]-3-pyrrolidinyl]-glycine, Ethyl Ester

HRID 2217917Notes

Reaction equation

HRID 2217917 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]3[C:13]([C:17]([NH:19][CH2:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[O:18])=[C:12]([Cl:27])[CH:11]=[CH:10][C:9]=3[N:8]=2)[CH2:3]1.Cl[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(N(CC)CC)C>C(#N)C>[Cl:27][C:12]1[C:13]([C:17]([NH:19][CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[O:18])=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:3]1)[CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 8471TriethylamineHCID 111766692-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide

Product 1

HCID 131726984N-[(3S)-1-[6-chloro-5-[[(cyclohexylmethyl)amino]carbonyl]-2-quinolinyl]-3-pyrrolidinyl]-glycine, Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 2-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide (prepared as in Example 44) (450 mg), ethyl chloroacetate (0.21 mL) and triethylamine (0.33 mL) in acetonitrile (3 mL) was heated at 100° C. in a microwave for 1 hour after which it was cooled to room temperature and concentrated. Purification by chromatography (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 96:3:1 as eluant) gave the subtitle compound as a solid (490 mg).

Workup

  1. concentrationconcentrated
  2. customPurification by chromatography (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 96:3:1 as eluant)

Sources & evidence

ORD record
ord-4f4f5d1fcae64909a06e71931385d2bd
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

Loading…