Triethylamine → HCID 178490316, compound

HRID 2253315Notes

Reaction equation

HRID 2253315 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[NH:10][C:9]=2[C:21]=1[C:22](O)=[O:23])(O)=[O:2].[NH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([O:47][CH3:48])[CH:40]=1)[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33].O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.CCN(CC)CC>C(O)CO.CCOC(C)=O.C(Cl)Cl>[CH3:48][O:47][C:41]1[CH:40]=[C:39]([CH2:38][CH2:37][N:29]([CH2:28][CH2:27][CH2:26][N:25]2[C:1](=[O:2])[CH2:4][C:5]3[CH:6]=[CH:7][C:8]4[N:12]=[C:11]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[O:19][CH3:20])[NH:10][C:9]=4[C:21]=3[C:22]2=[O:23])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH:44]=[CH:43][C:42]=1[O:45][CH3:46]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86601292HCID 86601292, compoundHCID 178489347HCID 178489347, compound

Product 1

HCID 178490316HCID 178490316, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 6-(carboxymethyl)-2-(2-methoxyphenyl)-1H-benzimidazole-7-carboxylic acid (800 mg, 2.45 mmol) and tert-butyl (3-aminopropyl)[2-(3,4-dimethoxyphenyl)ethyl]carbamate (1.00 g, 2.94 mmol) in ethyleneglycol (6.1 mL) was heated at 180° C. for 1 h. The cooled mixture was dissolved in EtOAc (500 mL) and the resulting solution was washed with water (2×100 mL) and brine (200 mL), dried (MgSO4) and concentrated under reduced pressure. A solution of the resulting yellow solid (1.04 g) and aqueous 1 N HCl solution (33 mL) in MeOH (100 mL) was heated at 70° C. for 16 h. The mixture was concentrated under reduced pressure. (BOC)2O (1.34 g, 6.12 mmol) and Et3N (2.06 g, 20.4 mmol) were successively added to a solution of the residue in CH2Cl2 (30 mL). The mixture was stirred at room temperature for 15 min then was diluted with CH2Cl2 (300 mL). The resulting solution was washed with water (2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 1:2 to 1:3) to give the title compound (839 mg, 54% yield) as a yellow solid.

Workup

  1. washthe resulting solution was washed with water (2×100 mL) and brine (200 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. concentrationThe mixture was concentrated under reduced pressure
  5. washThe resulting solution was washed with water (2×100 mL) and brine (100 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 1:2 to 1:3)

Sources & evidence

ORD record
ord-08c46ecd8aaa40b1a07dc2f3f7d90bd0
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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