Water → 6,6-dimethyl-2-(6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

HRID 885970Notes

Reaction equation

HRID 885970 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[CH2:14]C(C)(C)N[C:17](=O)[C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.[CH3:24][N:25]1[C:29]([CH3:30])=[C:28](B2OC(C)(C)C(C)(C)O2)[C:27]([CH3:40])=[N:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH2:49]>COCCOC.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>[CH3:5][C:6]1([CH3:23])[NH:7][C:14](=[O:49])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([C:28]5[C:27]([CH3:40])=[N:26][N:25]([CH3:24])[C:29]=5[CH3:30])[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27953111,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 685972362-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-one

Product 1

HCID 445807216,6-dimethyl-2-(6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-oneYield 34%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of Example 39 (0.055 g, 0.14 mmol), 1,3,5-trimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.066 g, 0.28 mmol), potassium phosphate (0.089 g, 0.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.05 g, 0.004 mmol) in DME (4 mL) and water (1 mL) was heated to 140° C. under microwave irradiation in a sealed tube for 30 minutes, and then concentrated in vacuo. Purification by preparative HPLC (Method 7) gave the title compound (0.020 g, 34%) as an off-white solid. δH (CDCl3) 7.84 (1H, d, J 1.9 Hz), 7.08-6.99 (2H, m), 5.45 (1H, s), 4.43-4.35 (2H, m), 4.22-4.16 (2H, m), 3.79 (3H, s), 2.87 (2H, s), 2.29 (6H, s), 1.40 (6H, s). LCMS (ES+) 424.0 (M+H)+, RT 3.17 minutes (Method 2).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by preparative HPLC (Method 7)

Sources & evidence

ORD record
ord-c1150b297da94ad091ae8d03558dcda0
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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