Benzenesulfonyl chloride → HCID 131733013, compound

HRID 2178365Notes

Reaction equation

HRID 2178365 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:28][C:29]([NH:31][C:32](=[O:36])[O:33][CH2:34][CH3:35])=S)[C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[C:12]([O:26][CH3:27])[CH:11]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.C1(S(Cl)(=O)=O)C=CC=CC=1>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]2[N:28]=[C:29]([NH:31][C:32](=[O:36])[O:33][CH2:34][CH3:35])[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[C:12]([O:26][CH3:27])[CH:11]=3)[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 118114077ethyl N-({5-iodo-2-[({3-methoxy-4-[(4-methoxyphenyl)methoxy]phenyl}methyl)amino]pyridin-3-yl}carbamothioyl)carbamate

Product 1

HCID 131733013HCID 131733013, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl N-({5-iodo-2-[({3-methoxy-4-[(4-methoxyphenyl)methoxy]phenyl}methyl)amino]pyridin-3-yl}carbamothioyl)carbamate (2.30 g, 3.69 mmol) and triethylamine (1.30 g, 1.8 mL, 12.85 mmol) in tetrahydrofuran (20 mL) was added benzenesulfonyl chloride (0.93 g, 5.27 mmol). The resulting mixture was allowed to stir at room temperature. After 12 h, a precipitate had formed. The mixture was filtered, and the filtercake was washed with water (2×10 mL) and methanol (10 mL). The solids were dried to provide 1.50 g (69%) of ethyl (6-iodo-3-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate as a brown solid.

Workup

  1. customa precipitate had formed
  2. filtrationThe mixture was filtered
  3. washthe filtercake was washed with water (2×10 mL) and methanol (10 mL)
  4. customThe solids were dried

Sources & evidence

ORD record
ord-77c10d483c854603b6272549f611977a
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

Loading…