4-Chlorobenzoic Acid → HCID 67235365, compound

HRID 2068557Notes

Reaction equation

HRID 2068557 reaction equation
[NH2:1][C:2]1([C:7]([NH:9][CH:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]3[CH:21]=[CH:22][N:23]=[C:11]23)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1.CCOC(C)=O>[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:1][C:2]2([C:7](=[O:8])[NH:9][CH:10]3[CH2:16][CH2:15][C:14]4[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=4[N:12]4[CH:21]=[CH:22][N:23]=[C:11]34)[CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:30])=[CH:27][CH:26]=1

Participants

8

Reactant 5

HCID 63184-Chlorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58304052HCID 58304052, compound

Product 1

HCID 67235365HCID 67235365, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-amino-N-(5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl)cyclopentanecarboxamide (158 mg, 509.02 μmoles), 4-chlorobenzoic acid (95.64 mg, 610.83 μmoles), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (117.10 mg, 610.83 μmoles), and 1-hydroxybenzotriazole (82.54 mg, 610.83 μmoles;) in tetrahydrofuran (12 mL). Add diisopropylethylamine (106.53 μL, 610.83 μmoles) and stir the reaction at ambient temperature for approximately 16 hours. Dilute the reaction with EtOAc, wash with dilute sodium bicarbonate and brine, dry over sodium sulfate, and concentrate the organic layer under reduced pressure. Purify the residue by flash chromatography (0-40% of a 5% solution of ammonia/methanol/dichloromethane (2N)/dichloromethane) to give the title compound (101.0 mg, 44%): MS (m/z): 449 (M+1).

Workup

  1. customthe reaction at ambient temperature for approximately 16 hours
  2. additionDilute
  3. washwash with dilute sodium bicarbonate and brine
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate the organic layer under reduced pressure
  6. customPurify the residue by flash chromatography (0-40% of a 5% solution of ammonia/methanol/dichloromethane (2N)/dichloromethane)

Sources & evidence

ORD record
ord-ce21b5eea5754bb38ea0436785ed0800
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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