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 1697419Notes

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 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 vacuo
customPurification (SiO2 chromatography eluting with 30-50% EtOAc in DCM)

Sources & evidence

ORD record: ord-36db1bc1baa841be8eda3e567d72b255
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163905B2

Reaction notes

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