Triethylamine → 6,6-Dimethyl-2-{6-[(2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885991Notes

Reaction equation

HRID 885991 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][CH2:16][N:15]([C:19]4[S:20][C:21]5[C:22](=[O:30])[NH:23][C:24]([CH3:29])([CH3:28])[CH2:25][C:26]=5[N:27]=4)[C:14]=3[CH:31]=2)[CH:3]=1.C(N(CC)CC)C>CO.[Pd]>[CH3:28][C:24]1([CH3:29])[NH:23][C:22](=[O:30])[C:21]2[S:20][C:19]([N:15]3[C:14]4[CH:31]=[C:10]([O:9][C:4]5[CH:3]=[CH:2][N:7]=[C:6]([CH3:8])[N:5]=5)[CH:11]=[CH:12][C:13]=4[O:18][CH2:17][CH2:16]3)=[N:27][C:26]=2[CH2:25]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 248558182-{6-[(6-Chloro-2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

Product 1

HCID 248558536,6-Dimethyl-2-{6-[(2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of Example 394 (40 mg, 0.088 mmol) in MeOH (15 mL) was added triethylamine (0.040 mL, 0.263 mmol) and 5% Pd/C (10 mg, 25% wt). The reaction mixture was stirred under an atmosphere of hydrogen for 24 h, then the catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL); the organic phase was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo to give the title compound (24 mg, 65%) as an off-white solid. δH (CDCl3) 8.45 (1H, d, J 5.8 Hz), 7.97 (1H, d, J 2.6 Hz), 6.98 (1H, d, J 8.9 Hz), 6.84 (1H, dd, J 8.9 and 2.6 Hz), 6.63 (1H, d, J 5.8 Hz), 5.58 (1H, s), 4.41-4.26 (2H, m), 4.16-4.05 (2H, m), 2.84 (2H, s), 2.62 (3H, s), 1.37 (6H, s). LCMS (ES+) 424.0 (M+H)+, RT 2.75 minutes (Method 1).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between DCM (50 mL) and water (50 mL)
  4. washthe organic phase was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-611fe985321c41e9bbb16998a11a8984
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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