1,2-Dichloroethane → HCID 66865001, compound

HRID 251874Notes

Reaction equation

HRID 251874 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([Cl:19])[CH:18]=1)[CH2:15][N:14]([CH3:20])[CH2:13][C@H:12]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:28]([CH2:30][O:31][CH2:32][C:33]([OH:35])=O)=[O:29].CCN(C(C)C)C(C)C.C(Cl)CCl>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([Cl:19])[CH:18]=1)[CH2:15][N:14]([CH3:20])[CH2:13][C@H:12]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[C:28](=[O:29])[CH2:30][O:31][CH2:32][C:33]1=[O:35]

Participants

5

Reactant 3

HCID 111,2-Dichloroethane2×HCID 81531Diisopropylethylamine2×HCID 66865118HCID 66865118, compound

Product 1

HCID 66865001HCID 66865001, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 {[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylcarbamoyl]-methoxy}acetic acid trifluoroacetic acid salt (50 mg) was dissolved in absolute dichloromethane (2 ml) with stirring and admixed with Hünig's base (46 μl). EDC (22 mg) was then added and the mixture was stirred at room temperature for several hours. After standing overnight, further EDC (22 mg) and Hünig's base (46 μl) were added. After 24 h, the solvent was removed and the residue purified by means of preparative HPLC. The product-containing fractions were combined, freed of acetonitrile and freeze-dried.

Workup

  1. stirringthe mixture was stirred at room temperature for several hours
  2. waitAfter 24 h
  3. customthe solvent was removed
  4. customthe residue purified by means of preparative HPLC
  5. customfreeze-dried

Sources & evidence

ORD record
ord-a89b2755de164149b0990ccf52d2818c
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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