Hydrochloric Acid → 2-(3'-Acetylamino-biphenyl-4-yloxymethyl)-thiazole-4-carboxylic acid

HRID 2113021Notes

Reaction equation

HRID 2113021 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[S:9][CH:10]=1)=[O:5])C.C(=O)([O-])[O-].[K+].[K+].[C:26]([NH:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)(=[O:28])[CH3:27].Cl>O.O1CCOCC1>[C:26]([NH:29][C:30]1[CH:35]=[C:34]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:8]3[S:9][CH:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]=3)=[CH:18][CH:17]=2)[CH:33]=[CH:32][CH:31]=1)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 576433502-(4-Iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl ester2×

Product 1

HCID 116030912-(3'-Acetylamino-biphenyl-4-yloxymethyl)-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A first stock solution was prepared consisting of 2-(4-iodo-phenoxymethyl) -thiazole-4-carboxylic acid ethyl ester (of intermediate 2; 1.56 g, 4 mmol), bis(tri -cyclohexyl-phosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 140 mg, 0.21 mmol), and dioxane (approximately 82 mL). A second stock solution was prepared consisting of potassium carbonate (1.66 g, 12 mmol) and water (approximately 8.2 mL). The solutions were sonicated and degassed by bubbling nitrogen gas through them. 4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction vial containing 3-acetamidobenzeneboronic acid (ASDI Incorporated, Newark, Del.; 107 mg, 0.6 mmol). The mixture was heated in a microwave oven at 170 degrees for 25 min. 1 M HCl (0.1 mL) was added to each vial, and the solution were passed through silica gel columns (1 g of silica), and washed with dimethylacetamide (2×1 mL). The solution was evaporated to dryness to give 2-(3′-acetylamino-biphenyl-4-yloxymethyl) -thiazole-4-carboxylic acid. Mass spectrum MH+=369.

Workup

  1. customA first stock solution was prepared
  2. customA second stock solution was prepared
  3. customThe solutions were sonicated
  4. customdegassed
  5. customby bubbling nitrogen gas through them
  6. addition4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction
  7. temperatureThe mixture was heated in a microwave oven at 170 degrees for 25 min
  8. washwashed with dimethylacetamide (2×1 mL)
  9. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-c1305f1710b34144b81017f0a3eefe8c
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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