Water → HCID 89761995, compound

HRID 528617Notes

Reaction equation

HRID 528617 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([S:27]([N:30]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[C:31]2[S:32][CH:33]=[CH:34][N:35]=2)(=[O:29])=[O:28])[CH:11]=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[O:25][CH3:26].Cl[CH2:46][C:47](Cl)=[O:48].O>CN(C=O)C>[CH3:26][O:25][C:16]1[CH:17]=[C:18]([C:21]([F:22])([F:23])[F:24])[CH:19]=[CH:20][C:15]=1[N:14]1[C:47](=[O:48])[CH2:46][O:7][C:8]2[CH:9]=[C:10]([S:27]([N:30]([CH2:36][C:37]3[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=3)[C:31]3[S:32][CH:33]=[CH:34][N:35]=3)(=[O:29])=[O:28])[CH:11]=[CH:12][C:13]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 10796Cesium carbonateHCID 89761246HCID 89761246, compound

Product 1

HCID 89761995HCID 89761995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 10-mL round bottom flask under N2 was dissolved cesium carbonate (807 mg, 2.48 mmol) and 3-hydroxy-4-((2-methoxy-4-(trifluoromethyl)phenyl)amino)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide (350 mg, 0.619 mmol) in 4 mL of DMF followed by a slow addition of chloroacetyl chloride (0.099 mL, 1.24 mmol) at rt. After 1 h the reaction mixture was neutralized with H2O and ice and the product 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide was collected as a solid and dried under reduced pressure and used directly in the next step.

Workup

  1. customthe product 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide was collected as a solid
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-702c5e0f82074cdb90aa6ed7dc6066d8
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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