Butoxyacetic acid → N-(Butoxyacetyl)-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

HRID 1644830Notes

Reaction equation

HRID 1644830 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:13]([O:17][CH2:18][C:19]([OH:21])=O)[CH2:14][CH2:15][CH3:16].[N:22]1([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:38]=[C:37]([CH2:39][CH:40]([CH3:42])[CH3:41])[S:36][C:35]=3[S:43]([NH2:46])(=[O:45])=[O:44])=[CH:30][CH:29]=2)[CH:26]=[CH:25][N:24]=[CH:23]1.C1CCN2C(=NCCC2)CC1>C1COCC1.CO>[CH2:13]([O:17][CH2:18][C:19]([NH:46][S:43]([C:35]1[S:36][C:37]([CH2:39][CH:40]([CH3:42])[CH3:41])=[CH:38][C:34]=1[C:31]1[CH:30]=[CH:29][C:28]([CH2:27][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:33][CH:32]=1)(=[O:44])=[O:45])=[O:21])[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 41958Butoxyacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 113947443(4-Imidazol-1-ylmethylphenyl)5-iso-butylthiophene-2 sulfonamide

Product 1

HCID 10163396N-(Butoxyacetyl)-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamideYield 21.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

CDI (1,1′-carbonyl-diimidazole, 129.5 mg, 0.80 mmol) was added to a solution of butoxyacetic acid (103.8 μL, 0.80 mmol) in dry THF (4 mL). The mixture was stirred at 50° C. for 2.5 h. A solution of 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide (see Example 1(f) above; 100 mg) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, 19.9 μL, 0.133 mmol) in dry THF (4 mL) was added to the reaction mixture. The reaction mixture was then stirred overnight at 50° C. MeOH (20 mL) was added to the reaction mixture, which was then concentrated in vacuo. The residue was dissolved in EtOAc (100 mL) and then washed with water (3×50 mL). The organic phase was dried and evaporated. The crude product was purified by column chromatography using 10% MeOH in CHCl3 as eluent to give the title compound (27 mg, 0.057 mmol).

Workup

  1. stirringThe reaction mixture was then stirred overnight at 50° C
  2. concentrationwas then concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with water (3×50 mL)
  5. customThe organic phase was dried
  6. customevaporated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b28c62df6dd14f25a97b1c3f718e8c99
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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