Potassium Carbonate → 5-[7-(2-Chloro-pyridin-4-yl)-imidazo[1,2-c]pyrimidin-5-yl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 729506Notes

Reaction equation

HRID 729506 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Cl:17])[CH:12]=2)[N:3]=1.[C:18]([N:25]1[CH2:30][C@@H:29]2[CH2:31][CH:26]1[CH2:27][NH:28]2)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[C:21]([O:20][C:18]([N:25]1[CH2:30][C@@H:29]2[CH2:31][C@H:26]1[CH2:27][N:28]2[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Cl:17])[CH:12]=2)[N:3]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 45073266(S)-N-Boc-2,5-Diaza-bicyclo[2.2.1]heptaneHCID 578326715-chloro-7-(2-chloro-4-pyridinyl)-Imidazo[1,2-c]pyrimidine

Product 1

HCID 866002915-[7-(2-Chloro-pyridin-4-yl)-imidazo[1,2-c]pyrimidin-5-yl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a 100 mL RBF was added 5-chloro-7-(2-chloro-pyridin-4-yl)-imidazo[1,2-c]pyrimidine (2.0 g, 7.6 mmol), 20 mL NMP, (S)—N-Boc-2,5-Diaza-bicyclo[2.2.1]heptane (1.6 g, 8.3 mmol), K2CO3 (1.05 g, 7.6 mmol) and DIEA (1.3 mL, 7.6 mmol). The mixture was stirred at rt under nitrogen for 15 h, and all starting material was converted. The reaction mixture was added to a 100 mL ice water slowly, and a white solid was precipitated out. The precipitate was filtrated and washed with 50 mL water, and further purified by flash chromatograph. The title compound was obtained. MS (ES+):427 (M+H)+.

Workup

  1. customa white solid was precipitated out
  2. filtrationThe precipitate was filtrated
  3. washwashed with 50 mL water
  4. customfurther purified by flash chromatograph

Sources & evidence

ORD record
ord-6bb04963d6be4be482797bb5e56a7413
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

Loading…