Ammonia → N-(2-amino-1-{[2-(2,6-dichlorophenyl)-6-quinolinyl]methyl}-2-oxoethyl)-2,6-dichlorobenzamide

HRID 1869805Notes

Reaction equation

HRID 1869805 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[C:4]([NH:6][CH:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:8](O)=[O:9])=[O:5].CC[N:37](CC)CC.ClC(OCC)=O.N>C1COCC1>[NH2:37][C:8](=[O:9])[CH:7]([NH:6][C:4](=[O:5])[C:3]1[C:30]([Cl:34])=[CH:31][CH:32]=[CH:33][C:2]=1[Cl:1])[CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:23]([Cl:29])=[CH:24][CH:25]=[CH:26][C:27]=1[Cl:28])[CH:16]=[CH:15]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10052832N-(2,6-dichlorobenzoyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alanine

Product 1

HCID 57987641N-(2-amino-1-{[2-(2,6-dichlorophenyl)-6-quinolinyl]methyl}-2-oxoethyl)-2,6-dichlorobenzamideYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acid 38 (2.12 g) in dry THF (15 ml) is cooled to −20° C. NEt3 (0.54 ml) and ethyl chloroformate (0.37 ml) are added. The solution is stirred at this temperature for 20 minutes. The resulting solution is saturated with gaseous NH3 at −30° C. The mixture is allowed to reach room temperature. After one night, the residue is filtered and washed with THF, then dried under vacuum at 60° C. and purified over silica gel using CH2Cl2/CH3OH (95/5) as eluent to give N-(2-amino-1-{[2-(2,6-dichlorophenyl)-6-quinolinyl]methyl}-2-oxoethyl)-2,6-dichlorobenzamide 122.

Workup

  1. customto reach room temperature
  2. waitAfter one night
  3. filtrationthe residue is filtered
  4. washwashed with THF
  5. customdried under vacuum at 60° C.
  6. custompurified over silica gel

Sources & evidence

ORD record
ord-26b8f2481b924fd79e8fb7d48c78e81d
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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