Hydrochloric Acid → HCID 16051278, compound

HRID 1591847Notes

Reaction equation

HRID 1591847 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([CH3:18])[C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[C:9]([C:21]#[N:22])[CH:8]=1.Cl>N1C=CC=CC=1>[C:21]([C:9]1[CH:8]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:12]=[CH:11][C:10]=1[C:13]1[N:17]([CH3:18])[C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)#[N:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 160505295-(4-Amino-2-cyanophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051278HCID 16051278, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methanesulfonyl chloride (0.074 mL, 1 mmol) and 5-(4-amino-2-cyanophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.166 g, 0.75 mmol) in pyridine (1 mL) was heated to 50° C. for 4 hours. The reaction mixture was acidified with 1N HCl solution and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethylacetate, 90/10 to 60/40) to afford the title compound (0.059 g, 33%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (hexane/ethylacetate, 90/10 to 60/40)

Sources & evidence

ORD record
ord-857aa4ff201a4ba2b8a6a7efa3692b48
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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