Hydrochloric Acid → 3-(pyrazol-1-yl)-2-methyl-4-(methylsulfonyl)-N-(1-methyltetrazol-5-yl)benzamide

HRID 448849Notes

Reaction equation

HRID 448849 reaction equation
S(Cl)(Cl)=O.[N:5]1([C:10]2[C:11]([CH3:23])=[C:12]([CH:16]=[CH:17][C:18]=2[S:19]([CH3:22])(=[O:21])=[O:20])[C:13](O)=[O:14])[CH:9]=[CH:8][CH:7]=[N:6]1.[CH3:24][N:25]1[C:29]([NH2:30])=[N:28][N:27]=[N:26]1.Cl>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.O>[N:5]1([C:10]2[C:11]([CH3:23])=[C:12]([CH:16]=[CH:17][C:18]=2[S:19]([CH3:22])(=[O:21])=[O:20])[C:13]([NH:30][C:29]2[N:25]([CH3:24])[N:26]=[N:27][N:28]=2)=[O:14])[CH:9]=[CH:8][CH:7]=[N:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 1384921-methyl-1H-tetrazol-5-amineHCID 666070373-(Pyrazol-1-yl)-2-methyl-4-(methylsulfonyl)benzoic acid

Product 1

HCID 666067853-(pyrazol-1-yl)-2-methyl-4-(methylsulfonyl)-N-(1-methyltetrazol-5-yl)benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

At RT, 178 mg (1.5 mmol) of thionyl chloride are added to 280 mg (1.0 mmol) of 3-(pyrazol-1-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, 148 mg (1.5 mmol) of 1-methyl-5-aminotetrazole and 12 mg (0.1 mmol) of DMAP in 2 ml of pyridine. The mixture is stirred at RT for 12 h and, after having been checked by LCMS, stirred at 50° C. for 3 h. 0.1 ml of water is then added, the mixture is stirred at RT for 30 min and 2N HCl is added. The product is filtered off with suction and dried. Yield 134 mg (37%).

Workup

  1. stirringstirred at 50° C. for 3 h
  2. stirringthe mixture is stirred at RT for 30 min
  3. filtrationThe product is filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-26c8fb94f7d8496aacadce31e78043c7
Source dataset
uspto-grants-2013_07
Patent number
US08481749B2

Reaction notes

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