Triethylamine → HCID 58016774, compound

HRID 1926934Notes

Reaction equation

HRID 1926934 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([O:18][CH:19]([CH3:23])[CH2:20][NH:21][CH3:22])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:37][O:38][C:39](=[O:44])[CH2:40][CH2:41][CH2:42]Br>ClCCl>[CH3:37][O:38][C:39](=[O:44])[CH2:40][CH2:41][CH2:42][N:21]([CH2:20][CH:19]([O:18][C:16]1[C:17]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[C:10]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:11][C:12]=2[N:13]=[CH:14][N:15]=1)[CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 107604Methyl 4-bromobutyrate2×HCID 58016851HCID 58016851, compound

Product 1

HCID 58016774HCID 58016774, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Put 25 mg (0.064 mmol) (+/−)-2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-N-methylpropane-1-amine with 13 mg (0.128 mmol) triethylamine in 250 μl dichloromethane. Add 23.2 mg (0.128 mmol) 4-bromobutyric acid methyl ester and stir overnight at RT. Add the same amounts of triethylamine and 4-bromobutyric acid methyl ester again and stir for a further 24 h at RT. Then concentrate by evaporation and purify the residue by thick-layer chromatography on silica gel (solvent: dichloromethane/methanol 95:5). Extract the product-containing zone with dichloromethane/methanol 9:1. 22.4 mg of the target compound is obtained as raw product.

Workup

  1. stirringstir for a further 24 h at RT
  2. concentrationThen concentrate by evaporation
  3. custompurify the residue by thick-layer chromatography on silica gel (solvent: dichloromethane/methanol 95:5)
  4. extractionExtract the product-containing zone with dichloromethane/methanol 9:1

Sources & evidence

ORD record
ord-1509af6ebf6a4bd38f96377328ceaeb4
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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