1,2-Dimethoxyethane → 2-(Benzo[d]furan-2-ylcarbonylamino)-4-benzothiazol-5-ylthiophene-3-carboxylic acid

HRID 387498Notes

Reaction equation

HRID 387498 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16](OS(C(F)(F)F)(=O)=O)[C:17]=1[C:18]([O:20]C(C)(C)C)=[O:19])=[O:11].C([O-])(O)=O.[Na+].CO[CH2:40][CH2:41]OC>CCO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:17]=[CH:16][C:15]3[S:14][CH:13]=[N:12][C:40]=3[CH:41]=2)[C:17]=1[C:18]([OH:20])=[O:19])=[O:11]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 59225740Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate

Product 1

HCID 461861472-(Benzo[d]furan-2-ylcarbonylamino)-4-benzothiazol-5-ylthiophene-3-carboxylic acidYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 7 (49 mg, 0.1 mmol) in 1,2-dimethoxyethane (DME, 2 mL) and EtOH (1 mL) was added 37 (31 mg, 0.12 mmol), 0.5 M NaHCO3 (1 mL). The suspension was bubbled with argon for 5 min before adding Pd(PPh3) (38, 12 mg, 0.01 mmol). The reaction mixture was heated at 110° C. for 30 min using microwave initiator. The solid was filtered off and the filtrate was extracted with EtOAc (10 ml×2). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The compound 39 was purified by HPLC. The 39 was dissolved in CH2Cl2 (2 ml) and TFA (0.5 ml) was added. The mixture was stirred for 2 h at r.t. The solvent was removed in vacuo. The residue was treated with MeOH (2 mL) and the solid was collected by centrifuge and washed with MeOH. Compound 40 (20 mg, 48%) was obtained as yellow solid. LC-MS: calcd. for C21H12N2O4S2: 419 (M−1).

Workup

  1. customThe suspension was bubbled with argon for 5 min
  2. filtrationThe solid was filtered off
  3. extractionthe filtrate was extracted with EtOAc (10 ml×2)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe compound 39 was purified by HPLC
  7. dissolutionThe 39 was dissolved in CH2Cl2 (2 ml)
  8. additionTFA (0.5 ml) was added
  9. customThe solvent was removed in vacuo
  10. additionThe residue was treated with MeOH (2 mL)
  11. customthe solid was collected by centrifuge
  12. washwashed with MeOH

Sources & evidence

ORD record
ord-4d3db1ecf991483abc5d688e7f22ae09
Source dataset
uspto-grants-2013_02
Patent number
US08372991B2

Reaction notes

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