Benzoic Acid → HCID 22170159, compound

HRID 1823311Notes

Reaction equation

HRID 1823311 reaction equation
C(O[C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([Cl:28])[CH:26]=3)[C:21]3=[N:29][O:30][C:31]([CH3:32])=[C:20]3[C:19]2=[O:33])[CH2:13]1)C1C=CC=CC=1.I[Si](C)(C)C.C(O)(=O)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C=O>[Cl:28][C:25]1[CH:26]=[C:27]2[C:22](=[N:23][CH:24]=1)[C:21]1=[N:29][O:30][C:31]([CH3:32])=[C:20]1[C:19](=[O:33])[N:18]2[CH:14]1[CH2:15][CH2:16][CH2:17][CH:12]([CH2:11][NH:10][C:9](=[O:34])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:13]1

Participants

9

Reactant 6

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 85247Trimethylsilyl iodideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10140698HCID 10140698, compound

Product 1

HCID 22170159HCID 22170159, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve [3-(7-chloro-3-methyl-4-oxo-5H-2-oxa-1,5,9-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester(70 mg, 0.15 mmol) in dry dichloromethane (5 mL). Add iodotrimethylsilane (0.05 mL, 0.35 mmol) and stir overnight at ambient temperature. Quench with methanol (5 mL) and concentrate in vacuo. Concentrate the resulting residue twice from diethyl ether and use directly without purification. Combine this amine salt with benzoic acid (22 mg, 0.18 mmol), 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (34 mg, 0.18 mmol), 1-hydroxy-7-azabenzo-triazole (24 mg, 0.18 mmol), and N,N-diisopropylethyl amine (0.10 mL, 0.57 mmol) in N,N-dimethylformamide (5 mL) and stir over a weekend at ambient temperature. Concentrate in vacuo and take up in water and extract with ethyl acetate. Dry the combined extracts over sodium sulfate and concentrate in vacuo. Elute the resulting residue over silica gel using ethyl acetate/dichloromethane to give 26 mg (38%) of the desired product as a white solid. MS(ES): (M+1)+ Exact Mass Calc'd: 451.1537. Found: 451.1554 m/z.

Workup

  1. customQuench with methanol (5 mL)
  2. concentrationconcentrate in vacuo
  3. concentrationConcentrate the resulting residue twice from diethyl ether and use
  4. customdirectly without purification
  5. concentrationConcentrate in vacuo
  6. extractionextract with ethyl acetate
  7. dry with materialDry the combined extracts over sodium sulfate
  8. concentrationconcentrate in vacuo
  9. washElute the resulting residue over silica gel

Sources & evidence

ORD record
ord-7e84553641be43a6944b856df427d8d8
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

Loading…