6-Aminohexanoic Acid → HCID 23627862, compound

HRID 1926916Notes

Reaction equation

HRID 1926916 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32].CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 5646-Aminohexanoic AcidHCID 962WaterHCID 81531DiisopropylethylamineHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 23627862HCID 23627862, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir 1.0 g (3.0 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, 0.78 g (5.94 mmol) 6-aminohexanoic acid and 1.5 ml DIEA in 10 ml DMF overnight at 120° C. Add the reaction mixture to water and extract three times with ethyl acetate. Combine the organic phases and wash with saturated sodium chloride solution, dry over magnesium sulphate and concentrate by vacuum evaporation. Chromatograph the residue on silica gel (solvent: cyclohexane/ethyl acetate 2:1→1:2). 560 mg (43.7% of theor.) of the target compound is obtained.

Workup

  1. extractionextract three times with ethyl acetate
  2. washwash with saturated sodium chloride solution
  3. dry with materialdry over magnesium sulphate
  4. concentrationconcentrate by vacuum evaporation
  5. custom560 mg (43.7% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-44986070d4e04613ab66743b5bc94887
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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