Hydrochloric Acid → HCID 58259952, compound

HRID 1020205Notes

Reaction equation

HRID 1020205 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH2:19]([C:22]1([S:25](Cl)(=[O:27])=[O:26])[CH2:24][CH2:23]1)[CH:20]=[CH2:21].Cl>N1C=CC=CC=1>[CH2:19]([C:22]1([S:25]([NH:1][C:2]2[C:3]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=3[F:18])=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)(=[O:27])=[O:26])[CH2:24][CH2:23]1)[CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chlorideHCID 58990848HCID 58990848, compound

Product 1

HCID 58259952HCID 58259952, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-4-(2-fluoro-4-iodophenylamino)-1-methylpyridin-2(1H)-one (prepared as described in steps a-e in example 1 above) was dissolved in dry pyridine at 0° C. under an ice-salt bath, and 1-allylcyclopropane-1-sulfonyl chloride was added. The resultant reaction mixture was allowed to warm to room temperature. After stirring for 16 hours at room temperature, aqueous HCl (1N) was added and the mixture was stirred for 15 minutes. The formed precipitate was filtered and dried under vacuum, and purified by preparative TLC (SiO2, EtOAc:MeOH=9:1 (v:v), Rf˜0.4).

Workup

  1. customThe resultant reaction mixture
  2. stirringthe mixture was stirred for 15 minutes
  3. filtrationThe formed precipitate was filtered
  4. customdried under vacuum
  5. custompurified by preparative TLC (SiO2, EtOAc:MeOH=9:1 (v:v), Rf˜0.4)

Sources & evidence

ORD record
ord-9636b797a1f14acca6573b2008d25429
Source dataset
uspto-grants-2014_05
Patent number
US08716318B2

Reaction notes

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