Benzoic Acid → HCID 22170170, compound

HRID 1823307Notes

Reaction equation

HRID 1823307 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:27]3[C:22](=[C:23]([Cl:28])[CH:24]=[N:25][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:40](O)(=[O:47])[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:23]1[CH:24]=[N:25][CH:26]=[C:27]2[C:22]=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:40](=[O:47])[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 69652769HCID 69652769, compound

Product 1

HCID 22170170HCID 22170170, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve [3-(9-chloro-3-methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester (310 mg, 0.64 mmol) in dry dichloromethane (8 mL). Add iodotrimethylsilane (0.23 mL, 1.62 mmol) and stir overnight at ambient temperature. Quench with methanol (5 mL) and concentrate in vacuo. Concentrate twice from diethyl ether and use the dark solid crude amine salt directly without purification. MS(ES): (M+1)+ 347.1 m/z. Combine this amine salt with benzoic acid (94 mg, 0.77 mmol),1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (148 mg, 0.77 mmol), 1-hydroxy-7-azabenzo-triazole (105 mg, 0.77 mmol), and N,N-diisopropylethyl amine (0.45 mL, 2.59 mmol), in N,N-dimethylformamide (8 mL) and stir over a weekend at ambient temperature. Concentrate in vacuo and take up in water and extract with dichloromethane. Dry over sodium sulfate and concentrate in vacuo. Elute over silica gel using methanol/dichloromethane to give 74 mg (26%) of the desired product as a white solid. MS(ES): (M+1)+ 451.1, 453.1 m/z.

Workup

  1. customQuench with methanol (5 mL)
  2. concentrationconcentrate in vacuo
  3. concentrationConcentrate twice from diethyl ether
  4. customdirectly without purification
  5. concentrationConcentrate in vacuo
  6. extractionextract with dichloromethane
  7. dry with materialDry over sodium sulfate
  8. concentrationconcentrate in vacuo
  9. washElute over silica gel

Sources & evidence

ORD record
ord-d1da8156fe064188bef40512b8638494
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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