Acetonitrile → HCID 24803453, compound

HRID 2094217Notes

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-4c6c8277f2ad4e53b516be504fa156ba
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445518B2

Reaction notes

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