Cesium carbonate → HCID 68181663, compound

HRID 1398675Notes

Reaction equation

HRID 1398675 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8](C(Cl)(Cl)Cl)[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.[OH:22][CH:23]1[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[NH2:20][C:16]1[N:15]=[C:14]([N:7]2[C:6]3[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[O:22][CH:23]2[CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26]2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 68181663HCID 68181663, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (1 g, 2.45 mmol), tert-butyl 3-hydroxyazetidine-1-carboxylate (2 g, 11.55 mmol) and cesium carbonate (4 g, 12.28 mmol) in N,N-dimethylformamide (15 mL) was stirred under nitrogen overnight at room temperature. The resulting solution was quenched with 200 mL of water. The precipitate was collected by filtration, washed with 200 mL of water and dried in a vacuum oven to give 750 mg (60%) of tert-butyl 3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidine-1-carboxylate as a yellow solid: LC-MS: m/z=+461 (M+H)+.

Workup

  1. customThe resulting solution was quenched with 200 mL of water
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with 200 mL of water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-acb10ccff01247a1aec9a8317ff530b6
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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