Cesium carbonate → HCID 57725408, compound

HRID 1922252Notes

Reaction equation

HRID 1922252 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:25][C:26]1[CH:31]=[C:30](F)[CH:29]=[CH:28][N:27]=1>CN1C(=O)CCC1>[Cl:25][C:26]1[CH:31]=[C:30]([O:18][C:16]2[CH:15]=[CH:14][C:12]3[N:13]=[C:9]([NH:8][C@@H:3]4[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]4[OH:1])[S:10][C:11]=3[CH:17]=2)[CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27827922-Chloro-4-fluoropyridineHCID 57725575HCID 57725575, compound

Product 1

HCID 57725408HCID 57725408, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

To the mixture of 2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (265 mg, 1 mmol) and cesium carbonate (651 mg, 2 mmol) in 3 ml of NMP was added 2-chloro-4-fluoropyridine (263 mg, 2 mmol). The reaction mixture was stirred at 60° C. for 20 hours. The crude reaction mixture was filtered and then purified on prep HPLC to give (1R,2R)-2-(6-(2-chloropyridin-4-yloxy)benzo[d]thiazol-2-ylamino)cyclohexanol as powder (341 mg, 0.9 mmol). ES/MS m/z 376.0 (MH+).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. custompurified on prep HPLC

Sources & evidence

ORD record
ord-32c3f6dc625949da87558f54835770ac
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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