Water → HCID 67157527, compound

HRID 549264Notes

Reaction equation

HRID 549264 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.[N:13]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[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:16]1[CH2:17][CH2:18][CH2:19][N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 67157527HCID 67157527, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Bromo-4-chloroquinoline (3.5 g, 14.5 mmol) was reacted with tert-butyl 1,4-diazepane-1-carboxylate (3.7 g, 18.8 mmol) and K2CO3 (4 g, 29 mmol) in DMSO at 100° C. overnight. After cooling the mixture was poured into water and extracted with DCM. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography using a gradient of EtOAc:hexane 1:1 to 2:1 giving 2.1 g (36%) of yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (d, J=5.5 Hz, 9H) 2.08-2.16 (m, 2H) 3.35-3.44 (m, 4H) 3.60-3-73 (m, 4H) 6.87 (d, J=5.5 Hz, 1H) 7.69 (dd, J=9.0, 2.0 Hz, 1H) 7.88 (d, J=8.5 Hz, 1H) 8.16 (s, 1H) 8.65 (d, J=5.0 Hz, 1H). MS (ESI+) for C19H24BrN3O2 m/z 406.4 (M+H)+. HRMS (EI) calcd for C19H24BrN3: 405.1052, found 405.1045.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with DCM
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0c163940d88a41a48c41ad392fac63a6
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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