Potassium Carbonate → HCID 178462999, compound

HRID 80863Notes

Reaction equation

HRID 80863 reaction equation
[Cl:1][C:2]1[C:3]([CH:47]2[CH2:49][CH2:48]2)=[N:4][N:5]([CH2:45][CH3:46])[C:6]=1[N:7]1[CH2:44][CH2:43][C:10]2[N:11]=[C:12]([C:22]3[C:30]([CH3:31])=[CH:29][CH:28]=[C:27]4[C:23]=3[C:24]([CH3:42])=[N:25][N:26]4S(C3C=CC(C)=CC=3)(=O)=O)[N:13]=[C:14]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[CH3:21])[C:9]=2[CH2:8]1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[C:3]([CH:47]2[CH2:48][CH2:49]2)=[N:4][N:5]([CH2:45][CH3:46])[C:6]=1[N:7]1[CH2:44][CH2:43][C:10]2[N:11]=[C:12]([C:22]3[C:30]([CH3:31])=[CH:29][CH:28]=[C:27]4[C:23]=3[C:24]([CH3:42])=[N:25][NH:26]4)[N:13]=[C:14]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[CH3:21])[C:9]=2[CH2:8]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 71244814HCID 71244814, compound

Product 1

HCID 178462999HCID 178462999, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (R)-4-(6-(4-chloro-3-cyclopropyl-1-ethyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylmorpholine (0.081 g, 0.116 mmol) in MeOH (3 mL) was added K2CO3 (0.080 g, 0.578 mmol). The mixture was heated at 55° C. for 1 h 30 min. The methanol was removed under reduced pressure and the residue was taken up in water and the aqueous phase was neutralized to pH=6 (with 3 N HCl) and then extracted with EtOAc (3×). The combined organic phases were washed with brine, dried with sodium sulfate, filtered and concentrated under reduce pressure. Purification by FCC (0-4% MeOH/DCM) provided the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.58 (s, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.21 (d, J=8.5 Hz, 1H), 4.33 (d, J=14.9 Hz, 1H), 4.18 (d, J=15.0 Hz, 1H), 3.90 (q, J=7.2 Hz, 2H), 3.87-3.82 (m, 1H), 3.81-3.74 (m, 1H), 3.67 (dd, J=11.2, 2.9 Hz, 1H), 3.63-3.42 (m, 4H), 3.39-3.31 (m, 1H), 3.00-2.93 (m, 2H), 2.18 (s, 3H), 1.88 (s, 3H), 1.84-1.73 (m, 1H), 1.29-1.21 (m, 3H), 1.14 (d, J=6.6 Hz, 3H), 0.89-0.81 (m, 4H), 0.80-0.73 (m, 1H); MS (ESI+) m/z 547.2 (M+H)+.

Workup

  1. customThe methanol was removed under reduced pressure
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by FCC (0-4% MeOH/DCM)

Sources & evidence

ORD record
ord-c146557f9f704f9cb1830089f1435c68
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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