Hydrazine → HCID 178509223, compound

HRID 706783Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:27])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[N:22][C:21]([C:24]#[N:25])=[C:20](Cl)[N:19]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:7]=1.[NH2:28][NH2:29]>CC(O)C.O>[NH2:25][C:24]1[C:21]2[C:20](=[N:19][C:18]([C:15]3[CH:16]=[CH:17][C:12]([NH:11][S:8]([C:6]4[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=4[F:27])(=[O:10])=[O:9])=[CH:13][CH:14]=3)=[CH:23][N:22]=2)[NH:29][N:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

5-Chloro-N-[4-(6-chloro-5-cyano-pyrazin-2-yl)-phenyl]-2-fluoro-benzenesulfonamide (160 mg) was suspended in a mixture of 1 ml iPrOH and 1 ml 35% hydrazine in water at RT and heated to 120° C. by microwave irradiation for 20 min under stirring in a sealed vessel. The reaction mixture was left to cool to RT and the crude reaction mixture was evaporated to dryness, redissolved in DMF and purified by preparative HPLC (C18 reversed phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were lyophilized to yield 38 mg (22%) of the title compound in the form of N-[4-(3-amino-1H-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-5-chloro-2-fluoro-benzenesulfonamide hydrochloride after lyophilizing with aqueous hydrogen chloride.

Workup

waitThe reaction mixture was left
temperatureto cool to RT
customthe crude reaction mixture
customwas evaporated to dryness
dissolutionredissolved in DMF
custompurified by preparative HPLC (C18
washphase column, elution with a water/MeCN gradient with 0.1% TFA)
additionThe fractions containing the product

Sources & evidence

ORD record: ord-928a516491bf4ce4b18dd563c69c0862
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174993B2

Reaction notes

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