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N,N-Dimethylglycine → (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(5-imidazol-1-yl-pyrimidin-2-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 409500
Notes
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Reaction equation

HRID 409500 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[C:14]2[N:19]=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH2:36][CH3:37])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:38]1[CH:42]=[CH:41][N:40]=[CH:39]1.C([O-])([O-])=O.[K+].[K+].CN(C)CC(O)=O.N.O>[Cu]I.CCOC(C)=O.CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[C:14]2[N:19]=[CH:18][C:17]([N:38]3[CH:42]=[CH:41][N:40]=[CH:39]3)=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH2:36][CH3:37])=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 673N,N-DimethylglycineHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 12896473Azane;hydrateHCID 59614321(2R,4S)-4-[(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59614380
(2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(5-imidazol-1-yl-pyrimidin-2-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
Yield 35%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 25 ml round-bottom tube is charged with (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (480 mg, 0.8 mmol), imidazole (82 mg, 1.2 mmol), CuI (152 mg, 0.8 mmol), K2CO3 (221 mg, 1.3 mmol), N,N-dimethyl glycine (82 mg, 0.8 mmol), and DMSO (4 ml). Then the tube is sealed and heated to 110 degree for 18 hours. After cooling to rt, saturated NH3/H2O and EtOAc are added and then filtered through Celite pad. The solution is extracted with EtOAc and organic layer is dried over MgSO4. Removal of solvent under reduced pressure and purification with reverse phase column give product (163 mg, 0.27 mmol, 35%). ESI-MS m/z: 585 [M]+, Retention time 2.07 min (condition A).

Workup

  1. customThen the tube is sealed
  2. temperatureheated to 110 degree for 18 hours
  3. filtrationfiltered through Celite pad
  4. extractionThe solution is extracted with EtOAc and organic layer
  5. dry with materialis dried over MgSO4
  6. customRemoval of solvent
  7. customunder reduced pressure and purification with reverse phase column

Sources & evidence

ORD record
ord-63e8d8a0ec744d69ad5c66b51f8ef850
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759365B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes