Water → HCID 57942446, compound

HRID 1898211Notes

Reaction equation

HRID 1898211 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=2)(=[O:14])=[O:13])[C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[NH2:26][C:27]1[CH:31]=[CH:30][NH:29][N:28]=1.O=P(Cl)(Cl)Cl.O>N1C=CC=CC=1>[N:29]1[NH:28][C:27]([NH:26][C:8]([C:5]2[C:4]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]([F:25])([F:23])[F:24])[CH:16]=3)(=[O:13])=[O:14])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:10])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 579420775-Chloro-3-(4-chloro-3-trifluoromethyl benzenesulfonylamino)-pyridine-2-carboxylic acidHCID 178418806HCID 178418806, compound

Product 1

HCID 57942446HCID 57942446, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 0° C. mixture of 5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid (41 mg, 0.1 mmol, 1 equiv) and 3-aminopyrazole (21 mg, 2.5 equiv) in 0.5 mL of pyridine was treated with 11 L (1.1 equiv) of POCl3 for 5 minutes. After addition of 1 mL of water, the mixture was subjected to preparative reverse phase HPLC to give 5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid (2H-pyrazol-3-yl)-amide. 1H NMR (400 MHz, CDCl3) δ 11.95 (s, 1H), 10.37 (s, 1H), 8.24 (m, 2H), 8.18 (s, 1H), 8.00 (dd, 1H), 7.63 (d, 1H), 7.60 (d, 1H), 6.80 (d, 1H); MS (ES) (M+H)+ expected 480.0. found 480.0.

Sources & evidence

ORD record
ord-f7d2e240df354809bb072790fd6e5750
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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