Phenylacetyl chloride → HCID 58034449, compound

HRID 1914838Notes

Reaction equation

[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].CCN(CC)CC.[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH3:15][O:14][C:12]([C:3]1[CH:4]=[N:5][C:6]2[N:7]([N:8]=[C:9]([CH3:11])[CH:10]=2)[C:2]=1[NH:1][C:30](=[O:31])[CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A 250 mL round-bottomed flask containing methyl 7-amino-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate (1.10 g, 5.0 mmol, 1 eq.), CH2Cl2 (40 mL), and Et3N (2.04 g, 20 mmol, 4 eq.) was added slowly phenylacetyl chloride (6.16 g, 40 mmol, 8 eq.). Then the mixture was heated at 80° C. for 4 h. The mixture was allowed to cool and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (40 mL) and water (25 mL). The aqueous phase was extracted with CH2Cl2 (2×15 mL). The combined organic solution was dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography using MeOH and CH2Cl2 as the mobile phases to furnish Compound (20-1) as a yellowish solid.

Workup

temperatureto cool
customthe solvent was removed in vacuo
dissolutionThe residue was dissolved in CH2Cl2 (40 mL)
extractionThe aqueous phase was extracted with CH2Cl2 (2×15 mL)
dry with materialThe combined organic solution was dried over Na2SO4
filtrationAfter filtration and concentration
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-e4319567ddcb4d98bb752bf998e86d7b
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614221B2

Reaction notes

Loading…