Cesium carbonate → HCID 59560283, compound

HRID 1643587Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:26]=[C:25]([OH:27])[C:19]3[CH2:20][C:21]([CH3:24])([CH3:23])[O:22][C:18]=3[CH:17]=2)=[O:15])=[N:9]1.Cl[CH2:29][CH:30]1[CH2:32][CH2:31]1>C(#N)C>[CH3:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:26]=[C:25]([O:27][CH2:29][CH:30]3[CH2:32][CH2:31]3)[C:19]3[CH2:20][C:21]([CH3:24])([CH3:23])[O:22][C:18]=3[CH:17]=2)=[O:15])=[N:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 60 mg of cesium carbonate (180 μmol) in a test tube (10×95 mm) was added 0.8 mL of 0.1 M solution of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carbo-xylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) in acetonitrile followed by 1 mL of 0.1 M solution of chloromethyl cyclopropane in acetonitrile and the reaction was stirred at 80° C. for 8 h. After the removal of solid cesium carbonate, the acetonitrile was removed, the residue was reconstituted in 1.2 mL of DMSO and subjected to HPLC purification to obtain the title compound. 1H NMR (500 MHz, DMSO-d6) δ 10.56 (s, 1 H) 7.57 (s, 1 H) 6.92 (s, 1 H) 6.54 (s, 1 H) 3.92-3.93 (d, J=5.00 Hz, 2 H) 2.94 (s, 2 H) 1.42 (s, 6 H) 0.55-0.60 (m, 2 H) 0.30-0.35 (m, 1H); LCMS for C19H23N3O3 m/z 342 (M+H)+.

Workup

customAfter the removal of solid cesium carbonate
customthe acetonitrile was removed
customsubjected to HPLC purification

Sources & evidence

ORD record: ord-d7fc137c51c943c09b739881f120ce24
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119624B2

Reaction notes

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