Tetrahydrofuran → HCID 178458415, compound

HRID 2236790Notes

Reaction equation

HRID 2236790 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.FC(F)(F)C(O)=O.[NH2:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH3:38])=[C:30]([CH:34]=1)[C:31]([OH:33])=[O:32].O1CCCC1.C(N(CC)CC)C>CN(C)C=O.O>[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]\[NH:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH3:38])=[C:30]([CH:34]=1)[C:31]([OH:33])=[O:32]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68696859HCID 68696859, compound

Product 1

HCID 178458415HCID 178458415, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (67 mg, 0.24 mmol) and 5-(aminomethyl)-2-propoxybenzoic acid trifluoroacetate (50 mg, 0.16 mmol) were coupled in N,N-dimethylformamide (2 mL) and tetrahydrofuran (2 mL) with triethylamine (0.13 mL). The mixture is heated at 50° C. for 30 minutes and then at 65° C. overnight. Water is added and resulting mixture purified by reverse-phase HPLC to give a white solid material which is collected by filtration, washed with water, methanol, and diethyl ether and then dried under house vacuum to give 5-({[(Z)-(6-bromo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)-2-propoxybenzoic acid (42 mg, 59%).

Workup

  1. customat 65° C.
  2. customovernight
  3. customresulting mixture
  4. custompurified by reverse-phase HPLC
  5. customto give a white solid material which
  6. filtrationis collected by filtration
  7. washwashed with water, methanol, and diethyl ether
  8. customdried under house vacuum

Sources & evidence

ORD record
ord-be123de2b94749f5bc6fb316a50abe21
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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