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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 2070841
Notes
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Reaction equation

HRID 2070841 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 13592063Benzyl (2-chloroethyl)methylcarbamateHCID 66689880N-cyclopropyl-3-{3-[2-(2-hydroxyphenyl)pyrrolidin-1-yl]-2-oxo-3,4-dihydropyrazin-1(2H)-yl]-4-methylbenzamide

Product 1

HCID 66689728Benzyl 2-(2-(1-(4-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-3-oxo-3,4-dihydropyrazin-2-yl)pyrrolidin-2-yl)phenoxy)ethyl(methyl)carbamate
Yield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

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

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. customthe solvent removed in is vacuo
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes