Acetic Acid → Lucitanib

HRID 1894308Notes

Reaction equation

HRID 1894308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][C:15]1([NH:18]C(=O)OCC3C=CC=CC=3)[CH2:17][CH2:16]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][C:36]=2[C:40](=[O:43])[NH:41][CH3:42])[CH:31]=1.C(O)(=O)C.Br.C(O)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[NH2:18][C:15]1([CH2:14][O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([O:29][C:30]4[CH:31]=[C:32]5[C:37](=[CH:38][CH:39]=4)[C:36]([C:40]([NH:41][CH3:42])=[O:43])=[CH:35][CH:34]=[CH:33]5)=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2][CH3:1])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 24905361HCID 24905361, compound

Product 1

HCID 25031915Lucitanib

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The product of Example 1 (100 mg) was mixed with acetic acid (1 ml) and 33% HBr/acetic acid (0.6 ml). The reaction was stirred at RT for 1 hour and diluted with EtOAc/H2O then basified with Na2CO3. The organic layer was dried, evaporated and purified with silica gel column to give the titled product. Mass: (M+1), 444

Workup

  1. customThe organic layer was dried
  2. customevaporated
  3. custompurified with silica gel column

Sources & evidence

ORD record
ord-ba51d87e3e5b49fb8cbe7fdc0624b9c6
Source dataset
uspto-grants-2013_08
Patent number
US08513283B2

Reaction notes

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