Potassium Carbonate → HCID 89761783, compound

HRID 528573Notes

Reaction equation

HRID 528573 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[OH:26].C([O-])([O-])=O.[K+].[K+].Cl[CH:34]([CH3:38])[C:35](Cl)=[O:36]>CN(C=O)C>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:11]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[S:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:35](=[O:36])[CH:34]([CH3:38])[O:26][C:3]=3[CH:4]=2)(=[O:9])=[O:10])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1110192-Chloropropionyl chlorideHCID 89761412HCID 89761412, compound

Product 1

HCID 89761783HCID 89761783, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-amino-3-hydroxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide (INTERMEDIATE AD) (2.0 g, 5.12 mmol) in DMF (15 mL) was added K2CO3 (2.1 g, 15.3 mmol, Quaigens). To the above suspension was added 2-chloropropanoyl chloride (0.780 g, 6.15 mmol) at 0° C. and reaction mixture was stirred at 25° C. for 30 min, then heated 60° C. for 3 h. The reaction mixture was cooled to 25° C. The organic compound was extracted with EtOAc, washed with water, dried over sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography using a gradient of 0-50% EtOAc in hexanes as the eluent to afford 1.45 g of N-(4-methoxybenzyl)-2-methyl-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as off white solid in 63.6% yield. 1H-NMR (400 MHz, DMSO): δ 7.45-7.46 (m, 2H), 7.40-7.44 (m, 1H), 7.23-7.26 (m, 3H), 7.02 (d, J=8.4 Hz, 1H), 6.85 (d, J=8.8 Hz, 2H), 5.19 (s, 2H), 3.70 (s, 3H), 1.44 (t, J=6.8 Hz, 3H); m/z (ESI, positive ion) 445.9 (M+H).

Workup

  1. customreaction mixture
  2. temperatureheated 60° C. for 3 h
  3. temperatureThe reaction mixture was cooled to 25° C
  4. extractionThe organic compound was extracted with EtOAc
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e21bf3adbe964b998baa604413c57e09
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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