Hydrochloric Acid → 1-(2,4-dichlorophenyl)-4-methyl-5-(4-iodophenyl)-N-(1,1-dioxothiomorpholino)-1H-pyrazole-3-carboxamide

HRID 532243Notes

Reaction equation

HRID 532243 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)=[C:12]([CH3:21])[C:11]([C:22](O)=[O:23])=[N:10]1.[NH2:25][N:26]1[CH2:31][CH2:30][S:29](=[O:33])(=[O:32])[CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl>O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)=[C:12]([CH3:21])[C:11]([C:22]([NH:25][N:26]2[CH2:31][CH2:30][S:29](=[O:33])(=[O:32])[CH2:28][CH2:27]2)=[O:23])=[N:10]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 127082634-Amino-1lambda~6~,4-thiazinane-1,1-dioneHCID 667612051-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 469129201-(2,4-dichlorophenyl)-4-methyl-5-(4-iodophenyl)-N-(1,1-dioxothiomorpholino)-1H-pyrazole-3-carboxamideYield 31.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The acid (7.5 g, 15.8 mmol) obtained from step D was taken in a 500 ml 1 neck flask equipped with a nitrogen inlet and to it 200 ml of DCM, 4-aminothiomorpholine-1,1-dioxide (2.61 g, 17.4 mmol), TBTU (5.59 g, 17.4 mmol) and DIPEA (2.25 g, 17.4 mmol) were added and the contents were stirred for 1 hour. To the reaction mixture, 100 ml of water was added and the contents were acidified to pH ˜2 using concentrated HCl. The organic layer was separated, washed with brine, dried over sodium sulphate and concentrated to give the amide (3 g, 31.2%).

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7009af71a4514617bd6ef1f444e1726c
Source dataset
uspto-grants-2014_10
Patent number
US08853205B2

Reaction notes

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