Triethylamine → HCID 10051708, compound

HRID 2292728Notes

Reaction equation

HRID 2292728 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[C:7]2[CH:29]=[C:30](C(O)=O)[CH:31]=[CH:32][C:6]=2[N:5]=1)[CH2:2][CH3:3].[C:36]([N:43]1[CH:47]=[CH:46][N:45]=[CH:44]1)(N1C=CN=C1)=O.C(N(CC)CC)C.CN[C:57]1[CH:63]=CC=[CH:60][C:58]=1N>O1CCCC1>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[C:17]([C:22]([OH:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:14][CH:15]=2)[C:7]2[CH:29]=[C:30]([C:44]3[N:43]([CH3:36])[C:47]4[CH:63]=[CH:57][CH:58]=[CH:60][C:46]=4[N:45]=3)[CH:31]=[CH:32][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 78498N-Methyl-o-phenylenediamineHCID 21479324HCID 21479324, compound

Product 1

HCID 10051708HCID 10051708, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 940 mg (2.0 mMol) of tert.-butyl 4'-[(2-n-propyl-6-carboxy-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylate and 320 mg (2.0 mMol) of carbonyldiimidazole in a solution of 1.0 ml of triethylamine in 30 ml of tetrahydrofuran is stirred for 30 minutes at ambient temperature, then 250 mg (2.0 mMol) of 2-methylaminoaniline are added and the mixture is stirred for a further 16 hours. It is then evaporated to dryness and the residue is refluxed in 20 ml of phosphorus oxychloride, with stirring, for 1 hour. The majority of the phosphorus oxychloride is then distilled off, the dark, greasy residue is decomposed with 30 ml of water, the strongly acidic suspension thus obtained is refluxed for about 1 hour, adjusted to pH 6 after cooling and then concentrated by evaporation. The crude product obtained is purified by column chromatography (120 g of silica gel, eluant: methylene chloride/methanol=15:1).

Workup

  1. stirringthe mixture is stirred for a further 16 hours
  2. customIt is then evaporated to dryness
  3. temperaturethe residue is refluxed in 20 ml of phosphorus oxychloride
  4. stirringwith stirring, for 1 hour
  5. distillationThe majority of the phosphorus oxychloride is then distilled off
  6. customthe strongly acidic suspension thus obtained
  7. temperatureis refluxed for about 1 hour
  8. temperatureafter cooling
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e4c2c2b1b8a947809a3ef94596c32ae3
Source dataset
uspto-grants-1997_11
Patent number
US05684029

Reaction notes

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