Tetramethyl orthocarbonate → HCID 21254765, compound

HRID 850171Notes

Reaction equation

HRID 850171 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([Cl:38])=[C:23]([C:34]([Cl:37])=[CH:35][CH:36]=2)[CH2:24][O:25][C:26]2[C:27]([NH2:33])=[C:28]([CH:30]=[CH:31][CH:32]=2)[NH2:29])[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:39](OC)(OC)(OC)[O:40][CH3:41]>C(O)(=O)C>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([Cl:38])=[C:23]([C:34]([Cl:37])=[CH:35][CH:36]=2)[CH2:24][O:25][C:26]2[C:27]3[N:33]=[C:39]([O:40][CH3:41])[NH:29][C:28]=3[CH:30]=[CH:31][CH:32]=2)[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 74613Tetramethyl orthocarbonateHCID 21254754HCID 21254754, compound

Product 1

HCID 21254765HCID 21254765, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-aminoaniline (735 mg) in acetic acid (7.4 ml) was added tetramethyl orthocarbonate (215 mg) at ambient temperature, and the mixture was stirred for 8 hours at the same temperature. The solvent was removed, and the residue was dissolved in chloroform. The solution was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (chloroform-methanol) to give 4-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1H-benzimidazole (654 mg).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with saturated sodium bicarbonate solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-3a966ebfa13741ddb08e0466aba64f75
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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