Dichloromethane → Benzyl 2-(2-(1-(4-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-3-oxo-3,4-dihydropyrazin-2-yl)pyrrolidin-2-yl)phenoxy)ethyl(methyl)carbamate

HRID 2070841Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[CH:7]1([NH:10][C:11](=[O:38])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N:19]3[CH:24]=[CH:23][NH:22][CH:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH:26]4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[OH:36])[C:20]3=[O:37])[CH:13]=2)[CH2:9][CH2:8]1.Cl[CH2:40][CH2:41][N:42]([CH3:53])[C:43](=[O:52])[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(Cl)Cl>C(#N)C.O>[CH:7]1([NH:10][C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH:26]4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH2:40][CH2:41][N:42]([CH3:53])[C:43](=[O:52])[O:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:20]3=[O:37])[CH:13]=2)=[O:38])[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 90 °C

Procedure

Cesium carbonate (0.274 g) was added to a solution of N-cyclopropyl-3-{3-[2-(2-hydroxyphenyl)pyrrolidin-1-yl]-2-oxo-3,4-dihydropyrazin-1(2H)-yl}-4-methylbenzamide (Example 324a, 0.18 g) and benzyl 2-chloroethyl(methyl)carbamate (0.096 g) in acetonitrile (4 mL), and the reaction was heated at 90° C. for 72 h. DCM and water were added, and the organic layer was separated, dried (Na2SO4) and the solvent removed in is vacuo. Purification (SiO2 chromatography eluting with 30-50% EtOAc in DCM) gave the subtitle compound as an oil (0.122 g).

Workup

customthe organic layer was separated
dry with materialdried (Na2SO4)
customthe solvent removed in is vacuo
customPurification (SiO2 chromatography eluting with 30-50% EtOAc in DCM)

Sources & evidence

ORD record: ord-5900c9177f734e8ab7dbd2fc49babfb3
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299246B2

Reaction notes

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