Cesium carbonate → HCID 57725629, compound

HRID 2370546Notes

Reaction equation

HRID 2370546 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+].[Br:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1Cl>CN1C(=O)CCC1>[Br:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[O:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([NH:8][C@@H:3]3[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]3[OH:1])[S:10][C:11]=2[CH:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 8176963-Bromo-4-chloropyridineHCID 57725575HCID 57725575, compound

Product 1

HCID 57725629HCID 57725629, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the reaction mixture of 2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (12.5 mg, 0.047 mmol) in 0.4 ml of NMP was added Cesium Carbonate (39 mg, 0.118 mmol) and stirred at RT for 1-3 minutes. To this mixture was added 3-bromo-4-chloropyridine (18.2 mg, 0.094 mmol). The reaction mixture was stirred at 90° C. for 4 hours or until done by LC. The crude reaction mixture was filtered, purified on prep HPLC and lyophilized to (1R,2R)-2-(6-(3-bromopyridin-4-yloxy)benzo[d]thiazol-2-ylamino)cyclohexanol as TFA salt (9.2 mg). ES/MS m/z 420.1/422.0 (MH+).

Workup

  1. stirringThe reaction mixture was stirred at 90° C. for 4 hours
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. custompurified on prep HPLC

Sources & evidence

ORD record
ord-8bb41fc555594fd08e69b812ba366986
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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