Triethylamine → HCID 178518277, compound

HRID 2236651Notes

Reaction equation

HRID 2236651 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.[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([OH:27])[C:21]=1[OH:28].CCN(CC)CC>CN(C)C=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:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([OH:27])[C:21]=1[OH:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dioneHCID 85797577HCID 85797577, compound

Product 1

HCID 178518277HCID 178518277, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (200 mg, 0.71 mmol) and 4-aminomethyl-benzene-1,2,3-triol hydrochloride salt (139.6 mg, 1 mmol) in N,N-dimethylformamide (DMF) (10 mL) is added Et3N (0.25 mL, 1.83 mmol). The resulting precipitate is filtered to give 83 mg (28.9%) of the title compound as a dark brown solid. (ESI) m/z 403.0 (M−H)−1. 1H NMR (DMSO-d6) δ 4.53 (d, 2H, J=6 Hz), 6.29 (d, 1H, J=8 Hz), 6.55 (d, 1H, J=8 Hz), 7.28 (d, 1H, J=8 Hz), 7.85 (d, 1H, J=8 Hz), 8.05 (s, 1H), 8.39 (s, 1H), 8.67 (d, 1H, J=12 Hz), 8.80 (s, 1H), 9.18 (s, 1H), 10.63-10.68 (m, 1H), 11.05 (s, 1H).

Workup

  1. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-09ca8e4c197e49e5a503a46130b9118b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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