Cesium carbonate → HCID 86619282, compound

HRID 1864003Notes

Reaction equation

HRID 1864003 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:18][CH3:19])[C:9]3[C:14]([OH:15])=[CH:13][N:12]=[C:11]([Cl:16])[C:10]=3[N:17]=2)=[N:4][O:5][N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][CH:28]1[S:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]1.[NH4+].[Cl-]>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:18][CH3:19])[C:9]3[C:14]([O:15][CH2:27][CH:28]4[S:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:29]4)=[CH:13][N:12]=[C:11]([Cl:16])[C:10]=3[N:17]=2)=[N:4][O:5][N:6]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 579738952-(4-Amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-7-olHCID 68662481HCID 68662481, compound

Product 1

HCID 86619282HCID 86619282, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound of intermediate VII (2.36 g, 8.40 mmol) in DMF (160 mL) was added anhydrous cesium carbonate (8.32 g, 25.0 mmol) and 1,1-dimethylethyl 2-(bromomethyl)-4-thiomorpholinecarboxylate (enantiomer E1) (2.50 g, 8.40 mmol). After stirring at ambient temperature for 4 h, sat NH4Cl was added and the reaction was extracted with EtOAc. The combined organic extracts were washed with water, brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue subjected to flash chromatography (MeOH/CH2Cl2, silica gel) to give the 2.3 g of the desired compound contaminated with 1,1-dimethylethyl 7-{[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-7-yl]oxy}tetrahydro-1,4-thiazepine-4-(5H)-carboxylate. This was used without further purification in the next step. MS (ES+) m/z 496 (M+H)+.

Workup

  1. additionwas added
  2. extractionthe reaction was extracted with EtOAc
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0597ba6a91054d668da9d207aa2a281a
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

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