1-methyl-1H-imidazole-4-sulfonyl chloride → HCID 66823139, compound

HRID 331683Notes

Reaction equation

HRID 331683 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([F:21])=[C:9]([CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]#[N:13])[CH:10]=1.[CH3:22][N:23]1[CH:27]=[C:26]([S:28](Cl)(=[O:30])=[O:29])[N:25]=[CH:24]1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:14]([CH:11]([C:12]#[N:13])[C:9]1[CH:10]=[C:5]([CH:6]=[CH:7][C:8]=1[F:21])[O:4][CH2:3][CH2:2][NH:1][S:28]([C:26]1[N:25]=[CH:24][N:23]([CH3:22])[CH:27]=1)(=[O:30])=[O:29])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 66747137HCID 66747137, compound

Product 1

HCID 66823139HCID 66823139, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-[5-(2-amino-ethoxy)-2-fluoro-phenyl]-3-phenyl-propionitrile (536 mg, 1.885 mmol) in dry dichloromethane was added 4-dimethylaminopyridine (345 mg, 2.83 mmol) followed by 1-methyl-1H-imidazole-4-sulfonyl chloride (409 mg, 2.262 mmol). The mixture was stirred at RT under argon over night. Dichloromethane was added and the mixture was subsequently washed twice with 1N hydrochloric acid, water, sodium bicarbonate solution, brine and then dried over sodium sulfate, filtered and concentrated to obtain the desired product as a pale yellow solid.

Workup

  1. washthe mixture was subsequently washed twice with 1N hydrochloric acid, water, sodium bicarbonate solution, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bbc08e9f95254927b17d6149b40eba31
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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