Barium hydroxide, octahydrate → Propane-2-sulfonic acid {2-[4'-(2h-tetrazol-5-ylmethyl)-biphenyl-4-yl]-thiophen-3-yl}-amide

HRID 746786

Reaction equation

HRID 746786 reaction equation
[N:1]1[CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16](OS(C(F)(F)F)(=O)=O)=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[N:4]=[N:3][N:2]=1.CC1(C)C(C)(C)OB(C2C=CC([C:41]3[S:42][CH:43]=[CH:44][C:45]=3[NH:46][S:47]([CH:50]([CH3:52])[CH3:51])(=[O:49])=[O:48])=CC=2)O1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>CN(C=O)C.O.CCOC(C)=O>[N:1]1[NH:2][N:3]=[N:4][C:5]=1[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:41]3[S:42][CH:43]=[CH:44][C:45]=3[NH:46][S:47]([CH:50]([CH3:52])[CH3:51])(=[O:49])=[O:48])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 17749109Barium hydroxide, octahydrateHCID 59747992Propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amideHCID 87753496trifluoro-methanesulfonic acid 4'-(5H-tetrazol-5-ylmethyl)-biphenyl-4-yl ester

Product 1

HCID 90710957Propane-2-sulfonic acid {2-[4'-(2h-tetrazol-5-ylmethyl)-biphenyl-4-yl]-thiophen-3-yl}-amideYield 56.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Deoxygenate and heat a mixture of trifluoro-methanesulfonic acid 4′-(5H-tetrazol-5-ylmethyl)-biphenyl-4-yl ester (48mg, 0.2 mmol), propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide (95 mg, 0.24 mmol, 1.2 eq.), barium hydroxide octahydrate(189 mg, 0.6 mmol, 3 eq.) and Pd(dffp)(29 mg, 0.04 mmol, 0.2 eq.) in 2 ml DMF and water mixture (4/1, v/v) to 80° C. overnight. Cool the mixture to room temperature and dilute with 30 mL EtOAc. Wash with water (3×10mL) and saturated aq. sodium chloride, dry, and remove solvent. Purification by flash chromatography (Silica gel-CH2Cl2:MeOH(1/50, v/v)) affords the title compound 50 mg(53%). MS (m/e): 441.1(M+1).

Workup

  1. customDeoxygenate
  2. temperatureheat
  3. customto 80° C.
  4. customovernight
  5. washWash with water (3×10mL) and saturated aq. sodium chloride
  6. customdry
  7. customremove solvent
  8. customPurification by flash chromatography (Silica gel-CH2Cl2

Sources & evidence

ORD record
ord-d758de596bda49fe87fcaad32f9a3042
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Linked notes

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