1,2-Dichloroethane → N-[4-(3-oxazolidinylcarbonyl)phenyl]-2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

HRID 1432544Notes

Reaction equation

HRID 1432544 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13](C(O)=O)[NH:12]2)=[O:10])=[CH:4][CH:3]=1.[O:24]1[CH2:28][CH2:27][N:26]([C:29](C2C=CC(N)=CC=2)=[O:30])[CH2:25]1.[CH2:38]([Cl:41])[CH2:39]Cl>CN(C=O)C>[O:24]1[CH2:28][CH2:27][N:26]([C:29]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9]([CH:11]3[CH2:20][C:15]4[C:14](=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:13][N:12]3[C:9]([NH:8][C:5]3[CH:6]=[CH:39][C:38]([Cl:41])=[CH:3][CH:4]=3)=[O:10])=[O:10])=[CH:6][CH:7]=2)=[O:30])[CH2:25]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 686942914-(3-Oxazolidinylcarbonyl)phenylamineHCID 131727716(4-Chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 11519028N-[4-(3-oxazolidinylcarbonyl)phenyl]-2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamideYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (50 mg, 0.15 mmol) and 4-(3-oxazolidinylcarbonyl)phenylamine (25 mg, 0.13 mmol) in DMF (3 mL), EDC (75 mg, 0.39 mmol) was added. The reaction mixture was stirred at room temperature overnight. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a white powder (26 mg). MS 505.2 and 507.2 (M+H, Cl pattern).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-06c1883e09cd4cef91389c8966ec0a9d
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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