Triethylamine → HCID 18354823, compound

HRID 429692Notes

Reaction equation

HRID 429692 reaction equation
C([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N:11]([CH3:35])[C:12](=[O:34])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[C:30]3[N:29]=[C:28]([CH3:31])[NH:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[O:21])=[C:15]([O:32][CH3:33])[CH:14]=1)(O)=O.C1(P([N:50]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>O1CCOCC1>[NH2:50][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N:11]([CH3:35])[C:12](=[O:34])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[C:30]3[N:29]=[C:28]([CH3:31])[NH:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[O:21])=[C:15]([O:32][CH3:33])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18355243HCID 18355243, compound

Product 1

HCID 18354823HCID 18354823, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(2-carboxy-4-methylphenyl)-3-methoxy-N-methyl-4-(2-methyl-1H-benzimidazol-4-yl)carbonylamino-benzamide (350 mg), diphenylphosphorylazide (224 mg) and triethylamine (82.5 mg) in dioxane (10 mg) was heated at 80° C. for 6 hours. After evaporation, the residual oil was subjected to silica gel column and the column was eluted with 5% methanol in chloroform. Object fractions were collected and evaporated in vacuo and the residue was solidified from chloroform to give N-(2-amino-4-methylphenyl)-3-methoxy-N-methyl-4-(2-methyl-1-H-benzimidazol-4-yl)carbonylamino-benzamide (280 mg).

Workup

  1. customAfter evaporation
  2. washthe column was eluted with 5% methanol in chloroform
  3. customObject fractions were collected
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-7e1264551db947eea92682a08762adfa
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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