4-Methylmorpholine → HCID 178425645, compound

HRID 351127Notes

Reaction equation

HRID 351127 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([NH2:8])=[NH:7].[Cl:13][C:14]1[CH:15]=[C:16]([S:21](Cl)(=[O:23])=[O:22])[CH:17]=[CH:18][C:19]=1[F:20].CN1CCOCC1>C1COCC1>[Cl:13][C:14]1[CH:15]=[C:16]([S:21]([NH:7][C:6](=[NH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH3:12])=[C:3]([F:2])[CH:4]=2)(=[O:22])=[O:23])[CH:17]=[CH:18][C:19]=1[F:20]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 166674393-Fluoro-4-methylbenzene-1-carboximidamide--hydrogen chloride (1/1)

Product 1

HCID 178425645HCID 178425645, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 3-fluoro-4-methylbenzamidine hydrochloride (0.025 g, 0.133 mmol) in THF (0.5 mL) to 3-chloro-4-fluorophenyl sulfonylchloride (0.0304 g, 0.133 mmol) followed by N-methylmorpholine (0.2 mL). The reaction mixture was concentrated and chromatographed using reverse phase chromatography (gradient of 5–95% (0.1% TFA in CH3CN) in (0.1% TFA in H2O). A white solid (16.4 mg, 36%) was isolated. ES Positive Ion MS [M+H]+ ions observed: m/z 345 (35Cl) and m/z 347 (37Cl).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-44a9351510d64d7b92f38cfef0672da9
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Reaction notes

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