Potassium Carbonate → HCID 66787466, compound

HRID 1947533Notes

Reaction equation

HRID 1947533 reaction equation
Cl[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[S:14][C:15]4[C:16]([N:21]=3)=[N:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][C:6]=2[O:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH:28]12[NH:35][CH:32]([CH2:33][CH2:34]1)[CH2:31][N:30]([C:36](=[O:38])[CH3:37])[CH2:29]2>CC#N.CN(C=O)C>[S:14]1[C:15]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[N:21]=[C:13]1[O:12][C:10]1[CH:9]=[CH:8][C:7]2[C:3]([CH2:2][N:35]3[CH:28]4[CH2:34][CH2:33][CH:32]3[CH2:31][N:30]([C:36](=[O:38])[CH3:37])[CH2:29]4)=[CH:4][O:5][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59577637HCID 59577637, compoundHCID 66787537HCID 66787537, compound

Product 1

HCID 66787466HCID 66787466, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a solution of 2-(3-chloromethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine (120 mg, 0.31 mmol) in CH3CN/DMF (4:1, 3 mL) was added K2CO3 (169 mg, 1.2 mmol) followed by 1-(3,8-diaza-bicyclo[3.2.1]oct-3-yl)-ethanone (47 mg, 0.31 mmol) and the reaction mixture was stirred (rt, 48 h). The reaction mixture was partitioned between DCM (10 mL) and sat. NaHCO3 (5 mL). The organic layer was separated and concentrated in vacuo. The resulting residue was purified by reverse phase HPLC to provide the title compound as a colorless solid (47 mg, 35%). MS (ESI): mass calcd. for C23H22N4O3S, 434.14; m/z found, 435.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.56 (dd, J=4.8, 1.7, 1H), 8.02 (dd, J=7.9, 1.7, 1H), 7.84 (d, J=8.5, 1H), 7.63-7.56 (m, 2H), 7.29 (dd, J=8.5, 2.1, 1H), 7.21 (dd, J=7.9, 4.8, 1H), 4.20 (dd, J=12.7, 1.5, 1H), 3.72-3.58 (m, 2H), 3.48-3.19 (m, 4H), 2.89 (d, J=12.3, 1H), 2.06 (s, J=2.8, 3H), 2.03-1.93 (m, 2H), 1.72-1.63 (m, 2H).

Workup

  1. customThe reaction mixture was partitioned between DCM (10 mL) and sat. NaHCO3 (5 mL)
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-75a89f7cf7f64329bc9cbcab84589f24
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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