Sodium Bicarbonate → 4-(2-cyanopropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide

HRID 1256410Notes

Reaction equation

HRID 1256410 reaction equation
[CH3:1][C:2]1[CH:17]=[C:5]2[N:6]=[C:7]([NH2:16])[CH:8]=[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:4]2[N:3]=1.[C:18]([C:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)([CH3:22])[CH3:21])#[N:19].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[C:18]([C:20]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([NH:16][C:7]2[CH:8]=[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:4]3[N:3]=[C:2]([CH3:1])[CH:17]=[C:5]3[N:6]=2)=[O:28])=[CH:30][CH:31]=1)([CH3:22])[CH3:21])#[N:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 450819154-(2-Cyanopropan-2-yl)benzoyl chlorideHCID 582071812-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine

Product 1

HCID 668789494-(2-cyanopropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamideYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 50 ml pear flask was added 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 450 mg, 2.0 mmol) in pyridine (10 ml). To this mixture was added 4-(2-cyanopropan-2-yl)benzoyl chloride (550 mg, 2.6 mmol) and the mixture was stirred at room temperature for 2 h. Saturated NaHCO3 was then added and pyridine was removed in vacuo. The residue was partitioned between saturated NaHCO3 and ethyl acetate, and the aqueous layer was extracted one more time with ethyl acetate. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, 15-25% EtOAc/hexanes) to give the titled compound (380 mg, 48%). 1H NMR (DMSO-d6) δ: 11.35 (s, 1H), 8.10-8.16 (m, 2H), 8.04-8.09 (m, 2H), 7.96 (s, 1H), 7.67-7.73 (m, 2H), 7.60-7.66 (m, 3H), 6.41 (s, 1H), 2.41 (s, 3H), 1.74 (s, 6H); ESI-MS: m/z 396.3 (M+H)+.

Workup

  1. custompyridine was removed in vacuo
  2. customThe residue was partitioned between saturated NaHCO3 and ethyl acetate
  3. extractionthe aqueous layer was extracted one more time with ethyl acetate
  4. dry with materialCombined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (SiO2, 15-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6eebfb511dbc4972a73fb6abbb25e6f1
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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