Potassium Carbonate → HCID 86618569, compound

HRID 2370555Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3C=CN=[C:14]([C:18]([NH:20][CH3:21])=O)[CH:13]=3)[CH:8]=[C:7]([CH3:22])[C:5]=2[N:6]=1.Br[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[C:31](=O)([O-])[O-].[K+].[K+].C[N:38]1[C:42](=[O:43])CCC1>>[CH:25]1([CH2:24][NH:1][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH2:12][C:13]4[CH:14]=[CH:18][N:20]=[C:21]([C:42]([NH2:38])=[O:43])[CH:31]=4)[CH:8]=[C:7]([CH3:22])[C:5]=3[N:6]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 13387N-methyl-2-pyrrolidone

HCID 137636Cyclohexane, (bromomethyl)-

HCID 57725436HCID 57725436, compound

Product 1

HCID 86618569HCID 86618569, compound

Conditions

Temperature: 80 °C

Procedure

To the solution of 4-(2-amino-4-methylbenzo[d]thiazol-6-yloxy)-N-methylpicolinamide (30 mg, 0.095 mmol, 1.0 eq) in 1 mL of NMP was added bromomethyl cyclohexane (20 μL, 0.142 mmol, 1.5 eq) and potassium carbonate (40 mg, 0.285 mmol, 3.0 eq) at room temperature. The reaction mixture was stirred at 80° C. for 12 hours and thereafter purified via reverse phase HPLC. LC/MS (m/z) [411.1] (MH+)

Workup

custompurified via reverse phase HPLC

Sources & evidence

ORD record: ord-18aff51883f64e0e981c5ee0cabe1144
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710048B2

Reaction notes

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