Water → 5-(1-(Benzo[D]thiazol-2-YL)piperidin-4-YL)-7,7-dimethyl-5H-pyrrolo[2,3-B]pyrazin-6(7H)-one

HRID 707394Notes

Reaction equation

HRID 707394 reaction equation
Cl.[CH3:2][C:3]1([CH3:19])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:4]1=[O:18].C(=O)([O-])[O-].[K+].[K+].Cl[C:27]1[S:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1.O>CS(C)=O>[S:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[N:15]1[CH2:16][CH2:17][CH:12]([N:5]2[C:6]3=[N:7][CH:8]=[CH:9][N:10]=[C:11]3[C:3]([CH3:19])([CH3:2])[C:4]2=[O:18])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 119872-ChlorobenzothiazoleHCID 866941487,7-Dimethyl-5-(piperidin-4-YL)-5H-pyrrolo[2,3-B]pyrazin-6(7H)-one hydrochloride2×

Product 1

HCID 866942595-(1-(Benzo[D]thiazol-2-YL)piperidin-4-YL)-7,7-dimethyl-5H-pyrrolo[2,3-B]pyrazin-6(7H)-oneYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7,7-dimethyl-5-(piperidin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one hydrochloride (Intermediate 78) (0.107 g, 0.378 mmol), potassium carbonate (0.183 g, 1.324 mmol), and 2-chlorobenzo[d]thiazole (0.077 g, 0.454 mmol) in DMSO (3 mL) was heated at 110° C. in 2 h. The reaction mixture was cooled, H2O was added, and extracted with DCM (3×). The organic extracts were dried over Na2SO4, filtered, concentrated, and purified by reverse phase HPLC. The pure fractions were concentrated to minimal H2O, neutralized with saturated aqueous NaHCO3. The white solid was collected, washed with H2O, and dried to afford the title compound (67 mg, 47%). MS (M+1): 380. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.04-8.19 (2 H, m), 7.77 (1 H, d, J=7.4 Hz), 7.46 (1 H, d, J=8.0 Hz), 7.21-7.35 (1 H, m), 6.98-7.14 (1 H, m), 4.46-4.65 (1 H, m), 4.18 (2 H, d, J=13.1 Hz), 3.32-3.41 (2 H, m), 2.52-2.62 (2 H, m), 1.83 (2 H, d, J=10.8 Hz), 1.33 (6 H, s)

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM (3×)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by reverse phase HPLC
  7. concentrationThe pure fractions were concentrated to minimal H2O
  8. customThe white solid was collected
  9. washwashed with H2O
  10. customdried

Sources & evidence

ORD record
ord-be48f53c58e24ec39390271732eeeca3
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…