Triethylamine → HCID 178505255, compound

HRID 2236915Notes

Reaction equation

HRID 2236915 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]=[C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[NH:13][C:12]2=[O:22])=[CH:5][CH:4]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>CN(C)C=O>[O:21]=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11](=[CH:10][NH:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][O:1][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:4][CH:5]=2)[C:12](=[O:22])[NH:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178518327HCID 178518327, compound

Product 1

HCID 178505255HCID 178505255, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of 4-[(4-Hydroxymethyl-phenylamino)-methylene]-4H-isoquinoline-1,3-dione (294 mg, 1 mmol) in N,N-dimethylformamide (10 mL) is added methanesulfonyl chloride (0.77 mL, 10 mmol) and triethylamine (2.79 mL, 20 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. The crude product, methanesulfonic acid 4-[(1,3-dioxo-2,3-dihydro-1H-isoquinolin-4-ylidenemethyl)-amino]-benzyl ester (304 mg), thus obtained is used as such for the next reaction.

Sources & evidence

ORD record
ord-5628bb13c07945b9a50fdfe988386949
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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