Cesium carbonate → 4-(3-Chloro-phenyl)-2-{4-methoxy-2-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenylamino}-thiazole-5-carboxylic acid amide

HRID 1667775Notes

Reaction equation

HRID 1667775 reaction equation
F[C:2]1[C:3]([N+:20]([O-:22])=[O:21])=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:17]=1)[O:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.[NH2:23][C:24]1[S:25][C:26]([C:36]([NH2:38])=[O:37])=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)[N:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C)C=O>[Cl:35][C:31]1[CH:30]=[C:29]([C:27]2[N:28]=[C:24]([NH:23][C:2]3[CH:17]=[C:6]([O:7][CH2:8][CH2:9][O:10][CH:11]4[CH2:16][CH2:15][CH2:14][CH2:13][O:12]4)[C:5]([O:18][CH3:19])=[CH:4][C:3]=3[N+:20]([O-:22])=[O:21])[S:25][C:26]=2[C:36]([NH2:38])=[O:37])[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 166588232-Amino-4-(3-chlorophenyl)thiazole-5-carboxamideHCID 67428436HCID 67428436, compound

Product 1

HCID 866428404-(3-Chloro-phenyl)-2-{4-methoxy-2-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenylamino}-thiazole-5-carboxylic acid amideYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.370 g of 2-[2-(5-fluoro-2-methoxy-4-nitro-phenoxy)-ethoxy]-tetrahydro-pyran (IV.44), 0.296 g (1.17 mmole) of 2-amino-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.2), 1.14 g (3.51 mmole) of cesium carbonate and 5 mL of dimethylformamide was heated at 70 degrees for 3 hours. The cooled mixture was poured into 30 mL of dilute ammonium chloride solution and the precipitated orange solid was collected by filtration, washed with water, and air-dried to give 0.470 g 4-(3-chloro-phenyl)-2-{4-methoxy-2-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenylamino}-thiazole-5-carboxylic acid amide (VI.44).

Workup

  1. temperaturewas heated at 70 degrees for 3 hours
  2. filtrationthe precipitated orange solid was collected by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-83f9de844faf4cf796b8f3bb26baefda
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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