Acetonitrile → HCID 24803453, compound

HRID 2245844Notes

Reaction equation

COC(OC)OC.[C:8](#N)C.[NH:11]1[CH:15]=[C:14]([NH2:16])[CH:13]=[N:12]1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[C:29]([C:35]([NH:37][NH2:38])=O)=[N:30][CH:31]=[C:32]([Cl:34])[CH:33]=2)(=[O:26])=[O:25])=[CH:20][C:19]=1[C:39]([F:42])([F:41])[F:40]>C(O)(=O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[C:29]([C:35]3[N:16]([C:14]4[CH:15]=[N:11][NH:12][CH:13]=4)[CH:8]=[N:38][N:37]=3)=[N:30][CH:31]=[C:32]([Cl:34])[CH:33]=2)(=[O:26])=[O:25])=[CH:20][C:19]=1[C:39]([F:42])([F:41])[F:40]

Participants

Conditions

Temperature: 120 °C

Procedure

The title compound was prepared according to general Method B. Thusly, a mixture of trimethylorthoformate (53 mg, 0.50 mmol), acetonitrile (1.5 mL), and 1H-pyrazol-4-ylamine (83 mg, crude, 1.0 mmol) was stirred at 120° C. for 2 hours. After the mixture was cooled to room temperature, 4-Chloro-N-(5-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide (42.8 mg, 0.10 mmol) and acetic acid (0.2 mL) was added and the resultant mixture was stirred at 120° C. for 2 hours. After evaporation of solvent under reduced pressure, the residue was further purified through automated normal-phase chromatography and dried (Lyophilizer) to afford title compound. 1H NMR: (DMSO-d6, ppm): 8.90 (s, 1H), 8.08 (m, 2H), 7.90 (m, 2H), 7.80 (m, 2H), 7.75 (m, 1H). MS (ES) [M+H]+ expected 504.0, found 504.0.

Workup

customThe title compound was prepared
temperatureAfter the mixture was cooled to room temperature
customAfter evaporation of solvent under reduced pressure
customthe residue was further purified
customdried (Lyophilizer)

Sources & evidence

ORD record: ord-06bbf606cc454cde8c2de7da49b78faa
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683176B2

Reaction notes

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