Triethylamine → HCID 178431207, compound

HRID 2236686Notes

Reaction equation

HRID 2236686 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.Cl.C([O:25][C:26]1[C:31]2[O:32][C:33]([CH3:36])([CH3:35])[O:34][C:30]=2[CH:29]=[C:28]([CH2:37][NH2:38])[CH:27]=1)C1C=CC=CC=1.C(N(CC)CC)C.[O-][Si]([O-])=O.[Mg+2]>CN(C)C=O.CO.C(Cl)(Cl)Cl>[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:38][CH2:37][C:28]1[CH:27]=[C:26]([OH:25])[C:31]2[O:32][C:33]([CH3:35])([CH3:36])[O:34][C:30]=2[CH:29]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 61680MAGNESIUM SILICATE (synthetic)HCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68699088HCID 68699088, compound

Product 1

HCID 178431207HCID 178431207, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.42 g, 1.5 mmol) and C-(7-benzyloxy-2,2-dimethyl-benzo[1,3]dioxol-5-yl)-methylamine hydrochloride (1.5 mmol) were coupled in N,N-dimethylformamide (10 mL) with triethylamine (0.6 mL). The crude material is dissolved in a minimum of 7.5% methanol in chloroform and then passed through a Florisil plug, eluting with 5% methanol in chloroform. The filtrate is concentrated under reduced pressure to give (4Z)-6-bromo-4-({[(7-hydroxy-2,2-dimethyl-1,3-benzodioxol-5-yl)methyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione as a light pink powder.

Workup

  1. washeluting with 5% methanol in chloroform
  2. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-6fdd613f376b4d3a978dde764b3dfd14
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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