Water → HCID 117668253, compound

HRID 64357Notes

Reaction equation

HRID 64357 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[C:3]=1[C:20]#[N:21].[N+:22]([C-:25]([CH:28]=O)[CH:26]=O)([O-:24])=[O:23].[Na+].O>CC(O)=O>[N+:22]([C:25]1[CH:26]=[N:1][C:2]2[N:6]([N:5]=[C:4]([C:7]3[CH:8]=[CH:9][C:10]([O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:11][CH:12]=3)[C:3]=2[C:20]#[N:21])[CH:28]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 111372352-Nitro-2-sodiopropanedialHCID 178509389HCID 178509389, compound

Product 1

HCID 117668253HCID 117668253, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (83 mg, 0.3 mmol) in HOAc (2 mL) was added sodium 2-nitro-1,3-dioxopropan-2-ide (47 mg, 0.3 mmol). After stirring at RT for 1 hr, water (2 mL) was added. The mixture was partitioned between EA (25 mL) and brine (25 mL). The combined organic layers were washed with brine (25 mL×2), dried over Na2SO4 and concentrated to afford 90 mg of 6-nitro-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (84%) as a yellow solid. MS (ESI) m/e [M+1]+ 358.2.

Workup

  1. customThe mixture was partitioned between EA (25 mL) and brine (25 mL)
  2. washThe combined organic layers were washed with brine (25 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-787ac79ae6cd417294b944c1e2743704
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

Loading…