Cesium carbonate → HCID 25119209, compound

HRID 2067186Notes

Reaction equation

HRID 2067186 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[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[CH:28][N:27]=1>CN1C(=O)CCC1>[N:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]([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)=[N:27][CH:28]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 788644-ChloroquinazolineHCID 57725575HCID 57725575, compound

Product 1

HCID 25119209HCID 25119209, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a reaction mixture of 2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (15.1 mg, 0.057 mmol; see Example 3 above) in 0.4 mL of NMP was added cesium carbonate (47 mg, 0.143 mmol) and stirred for 1-3 min at room temperature. To this mixture was added 4-chloroquinazoline (18.8 mg, 0.114 mmol). The reaction mixture was stirred at room temperature for 5 hours or until done by LC. The crude reaction mixture was filtered, purified by preparative HPLC, freebased, concentrated under reduced pressure and lyophilized to give the title compound (7.4 mg) as a solid. ES/MS m/z 393.2 (MHS, Rt=2.10 min.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 hours
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. custompurified by preparative HPLC
  5. concentrationfreebased, concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b10682794b44ed88fdc6d6546d8661c
Source dataset
uspto-grants-2012_10
Patent number
US08293769B2

Reaction notes

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