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Sodium Carbonate → 2-[6-(1,2-Dimethyl-1h-imidazol-4-yl)-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

HRID 885981
Notes
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Reaction equation

HRID 885981 reaction equation
[CH3:1][C:2]1([CH3:31])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19](B5OC(C)(C)C(C)(C)O5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:39]1[N:40]=[C:41]([CH3:45])[N:42]([CH3:44])[CH:43]=1>C1COCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:44][N:42]1[CH:43]=[C:39]([C:19]2[CH:20]=[CH:21][C:16]3[O:15][CH2:14][CH2:13][N:12]([C:10]4[S:9][C:5]5[C:6](=[O:8])[NH:7][C:2]([CH3:31])([CH3:1])[CH2:3][C:4]=5[N:11]=4)[C:17]=3[CH:18]=2)[N:40]=[C:41]1[CH3:45]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 72048754-Bromo-1,2-dimethyl-1H-imidazoleHCID 584916876,6-dimethyl-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

Product 1

HCID 671880512-[6-(1,2-Dimethyl-1h-imidazol-4-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneYield 14.4%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of Example 292 (75 mg, 0.17 mmol) in THF (3 mL) and water (1 mL) was added tetra-n-butylammonium bromide (107 mg, 0.34 mmol), sodium carbonate (36 mg, 0.34 mmol), 4-bromo-1,2-dimethyl-1H-imidazole (60 mg, 0.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol). The reaction was heated at 140° C. under microwave irradiation for 25 minutes. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative HPLC (Method 6) to yield the title compound (10 mg, 14%) as an off-white solid. δH (CDCl3) 8.09 (1H, d, J 2.1 Hz), 7.48 (1H, dd, J 8.5 and 2.1 Hz), 7.02 (1H, s), 6.95 (1H, d, J 8.5 Hz), 5.22 (1H, br. s), 4.36-4.29 (2H, m), 4.24-4.19 (2H, m), 3.60 (3H, s), 2.88 (2H, s), 2.42 (3H, s), 1.40 (6H, s). LCMS (ES+) 410.0 (M+H)+, RT 1.86 minutes (Method 1).

Workup

  1. customThe resulting mixture was partitioned between DCM (50 mL) and water (50 mL)
  2. washthe organic fraction was washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-48e18104b8c24bbe983ad6f36126d4d6
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242116B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes