Diisopropylethylamine → HCID 67309201, compound

HRID 1028057Notes

Reaction equation

HRID 1028057 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[NH:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 67309201HCID 67309201, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 6-bromo-4-chloroquinoline (1.0 equiv.), (S)-tert-butyl piperidin-3-ylcarbamate (1.0 equiv.) and DIEA (1.5 equiv.) in NMP (0.1 M) was heated at 140° C. for 48 hours. Upon cooling the solution was poured onto ice and upon melting the solid was filtered, rinsed with H2O and pumped on to yield (S)-tert-butyl 1-(6-bromoquinolin-4-yl)piperidin-3-ylcarbamate. LC/MS=406.0/408.0 (M+H), LC=2.85 min.

Workup

  1. temperatureUpon cooling the solution
  2. additionwas poured onto ice
  3. filtrationwas filtered
  4. washrinsed with H2O

Sources & evidence

ORD record
ord-0ae60dfa5ccf494b9d273f0b621666a0
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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