Triethylamine → HCID 11318693, compound

HRID 1271495Notes

Reaction equation

HRID 1271495 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][CH2:16][O:17][CH3:18])[C:3]1=[O:19].C1C([N+]([O-])=O)=CC=C([Cl-][C:30]([O-])=[O:31])C=1.C(N(CC)CC)C.[Cl:40][C:41]1[C:49]2[NH:48][C:47](=[O:50])[N:46]([CH:51]3[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]3)[C:45]=2[CH:44]=[CH:43][CH:42]=1>O1CCCC1>[Cl:40][C:41]1[C:49]2[NH:48][C:47](=[O:50])[N:46]([CH:51]3[CH2:56][CH2:55][N:54]([C:30]([NH:1][C@@H:2]4[CH2:8][CH2:7][C@@H:6]([C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=5)[CH2:5][N:4]([CH2:15][CH2:16][O:17][CH3:18])[C:3]4=[O:19])=[O:31])[CH2:53][CH2:52]3)[C:45]=2[CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 214934324-Chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 60037849(3R,6S)-3-Amino-1-(2-methoxyethyl)-6-phenylazepan-2-one

Product 1

HCID 11318693HCID 11318693, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R,6S)-3-amino-1-(2-methoxyethyl)-6-phenylazepan-2-one (0.015 g, 0.057 mmol) and 4-nitrophenylchloroformate (0.012 g, 0.057 mmol) in dry tetrahydrofuran (2 mL) was cooled to 0° C. under argon. Triethylamine (0.006 g, 0.057 mmol) was added and the reaction stirred for 1 h. Solid 4-chloro-1-piperidin-4-yl-1,3-dihydro-2H-benzimidazol-2-one (0.057 mmol) followed by triethylamine (0.055 g) were added. The reaction was allowed to come to room temperature and stirred for 1 h. The reaction was diluted with dicholoromethane and extracted with 1N NaOH until the yellow color of the organic layer disappeared. The organic layer was dried over sodium sulfate, concentrated and purified by normal phase chromatography (silica gel, 0 to 7% methanol in methylene chloride gradient elution), which gave the title compound (9 mg). MS 540.2370 (M+1).

Workup

  1. additionwere added
  2. customto come to room temperature
  3. stirringstirred for 1 h
  4. additionThe reaction was diluted with dicholoromethane
  5. extractionextracted with 1N NaOH until the yellow color of the organic layer
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by normal phase chromatography (silica gel, 0 to 7% methanol in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-0b6eb68ac9bb451dbbaf7a39caba40ab
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

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