gamma-Aminobutyric acid ethyl ester → HCID 58474408, compound

HRID 1400821Notes

Reaction equation

HRID 1400821 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[F:28])[CH:10]=2)=[N:7][CH:8]=1.[NH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=O.CCN(C(C)C)C(C)C>C(#N)C>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:10]=[C:9]([C:6]3[N:7]=[CH:8][C:3]([CH2:2][N:29]4[CH2:30][CH2:31][CH2:32][C:33]4=[O:35])=[CH:4][CH:5]=3)[S:17][C:16]=12

Participants

5

Reactant 3

HCID 23365gamma-Aminobutyric acid ethyl esterHCID 81531DiisopropylethylamineHCID 58474527HCID 58474527, compound

Product 1

HCID 58474408HCID 58474408, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 102 (500 mg, 1.202 mmol), ethyl 4-aminobutanoate (403 mg, 2.405 mmol) and DIPEA (0.630 mL, 3.61 mmol) under nitrogen in acetonitrile (12 mL) was heated to reflux for 3 days, then cooled to RT. The reaction mixture was then concentrated. The crude product was purified by Biotage (25M column; MeOH/DCM: 0/100 to 20/80 over 20 CV). The desired fractions were collected, concentrated and dried under high vacuum to afford the title compound 103 (270 mg, 0.58 mmol, 48% yield). MS (m/z): 465.5 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. concentrationThe reaction mixture was then concentrated
  4. customThe crude product was purified by Biotage (25M column; MeOH/DCM: 0/100 to 20/80 over 20 CV)
  5. customThe desired fractions were collected
  6. concentrationconcentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-7d8d74a650e141acaeae21b9bfb177b7
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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