Hydrochloric Acid → HCID 71179018, compound

HRID 2409290Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]3[N:15]=[CH:16][C:17]([S:18]([NH2:21])(=[O:20])=[O:19])=[C:13]3[N:12]=[CH:11][C:10]=2[C:22]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)=[O:23])=[C:4]([CH3:36])[CH:3]=1.[C:37](Cl)(=[O:39])[CH3:38].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]3[N:15]=[CH:16][C:17]([S:18]([NH:21][C:37](=[O:39])[CH3:38])(=[O:20])=[O:19])=[C:13]3[N:12]=[CH:11][C:10]=2[C:22]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:26][CH2:25]2)=[O:23])=[C:4]([CH3:36])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

7-(4-Fluoro-2-methylphenylamino)-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-sulfonamide (0.098 g, 0.175 mmol) obtained in Example 1 step 5 was dissolved in pyridine (2 mL), 4-(dimethylamino)pyridine (0.023 g, 0.189 mmol) and acetyl chloride (0.25 mL, 3.50 mmol) were added, and the mixture was stirred with heating at 50° C. for 2 hr. 1 mol/L Hydrochloric acid was added dropwise to the reaction mixture, and the mixture was extracted 3 times with chloroform. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give the title compound (0.013 g, 14%).

Workup

extractionthe mixture was extracted 3 times with chloroform
dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record: ord-8033f92da15e4ab49789a2012978747e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815874B2

Reaction notes

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