Diisopropylethylamine → (S)-2-(Quinazolin4-ylaminomethyl)-piperidine-1-carboxylic acid tert butyl ester

HRID 2113515Notes

Reaction equation

HRID 2113515 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClN1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19]C1.[CH:27]([N:30](C(C)C)CC)(C)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH:15][C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][N:30]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1502020tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylateHCID 866260114-Chloroquinoxaline

Product 1

HCID 86593670(S)-2-(Quinazolin4-ylaminomethyl)-piperidine-1-carboxylic acid tert butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.0 g), 4-chloroquinoxaline (0.768 g) and diisopropylethylamine (0.816 ml) were dissolved in tetrahydrofuran (75 ml) and heated to reflux for 6 hours under an atmosphere of argon. After cooling, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium hydrogen carbonate solution, saturated brine, dried and evaporated. The residue was chromatographed over silica gel, eluting with a gradient of 50 to 100% ethyl acetate in hexane. The title compound was obtained as a white foam (1.44 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours under an atmosphere of argon
  3. temperatureAfter cooling
  4. customthe reaction solution was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated sodium hydrogen carbonate solution, saturated brine
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed over silica gel
  9. washeluting with a gradient of 50 to 100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f013aa26b5834381bca8a1e5729c35f6
Source dataset
uspto-grants-2008_10
Patent number
US07432270B2

Reaction notes

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