Water → (+,-)-N-(cis-2-(5-Acetyl-2-fluoro-6-methoxymethoxyphenyl)cyclopropyl)-N'-(5-chloropyrid-2-yl)-urea

HRID 842651Notes

Reaction equation

HRID 842651 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9]OCCCC)=[C:4]([O:15][CH2:16][O:17][CH3:18])[C:3]=1[C@H:19]1[CH2:21][C@H:20]1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1)=[O:24].[OH2:33]>O1CCOCC1.Cl>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@H:19]2[CH2:21][C@H:20]2[NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)=[O:24])[C:4]=1[O:15][CH2:16][O:17][CH3:18])(=[O:33])[CH3:9]

Participants

5

Reactant 2

HCID 962WaterHCID 69934073HCID 69934073, compound

Product 1

HCID 22940407(+,-)-N-(cis-2-(5-Acetyl-2-fluoro-6-methoxymethoxyphenyl)cyclopropyl)-N'-(5-chloropyrid-2-yl)-urea

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

(+,−)-N-(cis-2-(2-fluoro-5-butoxyvinyl-6-methoxymethoxy)-cyclopropyl)-N′-(5-chloropyrid-2-yl)-urea (Example 55) was dissolved in dioxane and a few drops of dilute hydrochloric acid was added. The solution was stirred for 15 minutes, was diluted water and evaporated. The residue was co-evaporated with water to yield the title product as a solid. 1H-NMR CDCl3 1.3 (q, 1H) 1.5 (q, 1H) 2.1 (q, 1H) 2.5 (s, 3H) 3.4 (m, 1H) 3.5 (s, 3H) 5.1 (m, 2H) 6.8 (m, 2H) 7.4-7.6 (m, 2H) 7.8 (d, 1H) 9.1 (bs, 1H) 9.8 (bs, 1H).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-7957ee427f974efab4b367128922eaf3
Source dataset
uspto-grants-2002_04
Patent number
US06376492B1

Reaction notes

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