Potassium Carbonate → HCID 178496659, compound

HRID 80842Notes

Reaction equation

HRID 80842 reaction equation
[Cl:1][C:2]1[C:3]([CH:49]2[CH2:51][CH2:50]2)=[N:4][N:5]([CH3:48])[C:6]=1[N:7]1[CH2:47][CH2:46][C:10]2[N:11]=[C:12]([C:25]3[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]4[C:26]=3[C:27]([CH3:45])=[N:28][N:29]4S(C3C=CC(C)=CC=3)(=O)=O)[N:13]=[C:14]([N:15]3[CH2:20][CH2:19][C@@H:18]([O:21][CH3:22])[C:17]([CH3:24])([CH3:23])[CH2:16]3)[C:9]=2[CH2:8]1.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH:49]2[CH2:50][CH2:51]2)=[N:4][N:5]([CH3:48])[C:6]=1[N:7]1[CH2:47][CH2:46][C:10]2[N:11]=[C:12]([C:25]3[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]4[C:26]=3[C:27]([CH3:45])=[N:28][NH:29]4)[N:13]=[C:14]([N:15]3[CH2:20][CH2:19][C@@H:18]([O:21][CH3:22])[C:17]([CH3:24])([CH3:23])[CH2:16]3)[C:9]=2[CH2:8]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 71244805(R)-6-(4-Chloro-3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Product 1

HCID 178496659HCID 178496659, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-6-(4-chloro-3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (0.050 g, 0.068 mmol) in MeOH (3 mL) was added K2CO3 (0.057 g, 0.410 mmol). The mixture was heated at 55C. under a nitrogen atmosphere for 2 h. At that point the mixture was diluted with EtOAc and washed with sat aq NH4Cl and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by FCC (0-10% MeOH/DCM) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.59 (s, 1 H), 7.39 (d, J=8.3 Hz, 1 H), 7.21 (d, J=8.8 Hz, 1 H), 4.39 (d, J=14.9 Hz, 1 H), 4.25 (d, J=14.7 Hz, 1 H), 3.62-3.78 (m, 1 H), 3.56 (s, 3 H), 3.46-3.55 (m, 2 H), 3.30 (d, J=3.5 Hz, 1 H), 3.26 (s, 3 H), 2.99-3.08 (m, 1 H), 2.97 (dd, J=9.1, 4.0 Hz, 1 H), 2.92 (app. t, J=5.9 Hz, 2 H), 2.85 (d, J=12.9 Hz, 1 H), 2.18 (s, 3 H), 1.85-1.96 (m, 4 H), 1.74-1.82 (m, 1 H), 1.49-1.60 (m, 1 H), 0.92 (s, 3 H), (overlapped m, 2 H), 0.81 (s, 3H), 0.72-0.77 (m, 2 H); MS (ESI+) m/z 575.5 (M+H)+.

Workup

  1. washwashed with sat aq NH4Cl
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by FCC (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-b99f95562fd44447b25b88686cafb3be
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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