Sodium Chloride → CID 86717314

HRID 588617Notes

Reaction equation

[N:1]([O-])=O.[Na+].[CH]Cl.[F:7][C:8]1[CH:9]=[C:10]([C:14]2[C:18]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:17]([NH2:27])[NH:16][N:15]=2)[CH:11]=[CH:12][CH:13]=1.[Na+].[Cl-:29]>C(Cl)Cl>[Cl:29][C:19]1[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:1][N:27]=[C:17]2[NH:16][N:15]=[C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([F:7])[CH:9]=3)[C:18]=12

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium nitrite (740 mg, 10.7 mmol) was added portionwise to cHCl (24 mL) at −15° C. and stirred for 15 min. 3-(3-fluorophenyl)-4-(2-phenylethynyl)-1H-pyrazol-5-amine (1 g, 3.6 mmol) was added as a solid, followed by the addition of CH2Cl2 (10 mL). The reaction mixture was allowed to warm up and stirred at room temperature for 1.5 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and NaCl (0.5 g) was added. The reaction mixture was heated to 50° C. for 1 d. The layers were separated and the organic layer was washed with water, dried (phase separator cartridge) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 0:1 to 7:3) yielding the title compound as a solid (500 mg).

Workup

temperatureto warm up
stirringstirred at room temperature for 1.5 h
additionwas added
customThe layers were separated
washthe organic layer was washed with water
customdried (phase separator cartridge)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 0:1 to 7:3)

Sources & evidence

ORD record: ord-56e22d458b5147dd91105ec2bef09a1d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227976B2

Reaction notes

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