2-Amino-4,6-dimethoxy-1,3,5-triazine → beta-Methoxyethyl 6-fluoro-2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate

HRID 1030005

Reaction equation

[F:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9])=[C:6]([S:15]([N:18]=[C:19]=[O:20])(=[O:17])=[O:16])[CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[N:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([O:30][CH3:31])[N:23]=1>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9])=[C:6]([S:15]([NH:18][C:19]([NH:21][C:22]2[N:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([O:30][CH3:31])[N:23]=2)=[O:20])(=[O:16])=[O:17])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

7.1 g of β-methoxyethyl 6-fluoro-2-isocyanatosulfonylbenzoate in 20 ml of methylene chloride were added over 10 minutes at 25° C. to a stirred mixture of 4 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 40 ml of DMF under nitrogen; the temperature rose to 32° C. After the mixture had been stirred for 14 hours at 25° C., the solvent was removed under reduced pressure and the residue was stirred with ether and twice with 3N HCL. It was then taken up in acetone, insoluble mater was separated off and the filtrate was concentrated to dryness. 7 g of the compound shown in the title, of melting point 179° C.-182° C. were obtained.

Workup

customrose to 32° C
customthe solvent was removed under reduced pressure
stirringthe residue was stirred with ether and twice with 3N HCL
custominsoluble mater was separated off
concentrationthe filtrate was concentrated to dryness
customwere obtained

Sources & evidence

ORD record: ord-5e8fc6275902491a8fa4bdc122d4fc4e
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104441

Linked notes

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