Dimethylformamide → HCID 178465372, compound

HRID 2236741Notes

Reaction equation

HRID 2236741 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.CN(C)C=O.[NH2:22][C:23]([C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1)([CH3:27])[C:24]([OH:26])=[O:25]>CCOCC>[NH2:22][C:23]([C:28]1[CH:29]=[CH:30][C:31]([NH:34][CH:14]=[C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[C:8](=[O:12])[NH:7][C:6]2=[O:13])=[CH:32][CH:33]=1)([CH3:27])[C:24]([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19751636HCID 19751636, compoundHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178465372HCID 178465372, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (191 mg, 0.50 mmole), N,N-dimethylformamide (2 mL) and 2-Amino-2-(4-amino-phenyl)-propionic acid (90 mg, 0.50 mmole) is stirred and heated at 110° C. for one hour, cooled in the refrigerator. The reaction mixture is diluted with ether, filtered, washed with acetonitrile and dried to give a dull yellow solid 71 mg (33%), mp 250-253° C.; MS (ESI): m/z 428.2, 430.2 (M−H).

Workup

  1. temperaturecooled in the refrigerator
  2. filtrationfiltered
  3. washwashed with acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-98e864a34d614207957a9cc3b3235df6
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…