Triethylamine → HCID 86679344, compound

HRID 1498915Notes

Reaction equation

HRID 1498915 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][C:10]([CH2:14][OH:15])=[C:11]([CH3:13])[N:12]=1.[CH3:16][N:17]1[C:21]2[CH:22]=[CH:23][C:24](C(O)=O)=[CH:25][C:20]=2[N:19]=[CH:18]1.C([N:31]([CH2:34]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:13][C:11]1[N:12]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[S:9][C:10]=1[CH2:14][O:15][C:34](=[O:43])[NH:31][C:24]1[CH:23]=[CH:22][C:21]2[N:17]([CH3:16])[CH:18]=[N:19][C:20]=2[CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 49130631-Methyl-1H-benzimidazole-5-carboxylic acidHCID 16495169HCID 16495169, compound

Product 1

HCID 86679344HCID 86679344, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene (3 ml), [2-(2-methylphenyl)-4-methylthiazol-5-yl]methanol (80 mg, 0.37 mmol) prepared in Example 12-2 and 1-methyl-1H-benzimidazole-5-carboxylic acid (77 mg, 0.44 mmol) prepared in Example 11-1 were suspended, and triethylamine (48 mg, 0.47=1) and then diphenylphosphoryl azide (0.12 g, 0.44 mmol) were added thereto. The mixture was heated under reflux for one hour. After being allowed to cool, the mixture was purified by silica gel column chromatography (ethyl acetate:methanol=20:1) to give the title compound (0.11 g, 75%) as a light-brown powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. temperatureto cool
  4. customthe mixture was purified by silica gel column chromatography (ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-5115dbdce66944d18b405d84fe317fce
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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