2-Methylpyridine → N-[2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetyl]sulfamic acid

HRID 1271313Notes

Reaction equation

HRID 1271313 reaction equation
N1C=CC=CC=1C.Cl[S:9]([OH:12])(=[O:11])=[O:10].[C:13]1([C:19]2[N:20]=[CH:21][C:22]([N:31]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]([NH2:43])=[O:42])[CH:32]([CH3:34])[CH3:33])=[N:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl.ClCCl>[C:13]1([C:19]2[N:20]=[CH:21][C:22]([N:31]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]([NH:43][S:9](=[O:11])(=[O:10])[OH:12])=[O:42])[CH:32]([CH3:34])[CH3:33])=[N:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 79752-MethylpyridineHCID 24638Chlorosulfonic acidHCID 184526472-[4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy]acetamide

Product 1

HCID 18452623N-[2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetyl]sulfamic acid

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

Under an argon atmosphere, a solution of 1.443 g of 2-picoline in 1.7 ml of 1,2-dichloroethane was cooled to −10° C. A solution of chlorosulfonic acid in 3.5 ml of 1,2-dichloroethane was added dropwise at 0° C. or lower and, after stirring for 15 minutes, 712 mg of 2-[4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy]acetamide was added. The reaction solution was heated to 75° C. and air-cooled to room temperature after stirring for 2 hours. The reaction solution was diluted with dichloromethane and then washed in turn with an aqueous 0.6M sodium hydrogen sulfate and water. The reaction solution was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 798 mg of N-[2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetyl]sulfamic acid.

Workup

  1. temperatureair-cooled to room temperature
  2. stirringafter stirring for 2 hours
  3. washwashed in turn with an aqueous 0.6M sodium hydrogen sulfate and water
  4. dry with materialThe reaction solution was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-499cc722778d4455ab7262954f47a3c4
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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