Cyclobutanol → HCID 131731327, compound

HRID 2366916Notes

Reaction equation

HRID 2366916 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[C@H:7]([NH2:15])[CH2:6][C@@H:5]1[CH3:16])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.C1[C:31]([N+]([O-])=O)=[CH:30][CH:29]=[C:28]([O:35][C:36](Cl)=[O:37])C=1.C1(O)CCC1>ClCCl>[CH:28]1([O:35][C:36](=[O:37])[NH:15][C@H:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=3)[N:4]([C:1](=[O:3])[CH3:2])[C@@H:5]([CH3:16])[CH2:6]2)[CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 76218CyclobutanolHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 67194540cis-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine

Product 1

HCID 131731327HCID 131731327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(cis)-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 4) (200 mg, 0.706 mmol) was dissolved in dichloromethane (DCM) (5 mL), mixed with DIPEA (0.370 mL, 2.119 mmol) followed by 4-nitrophenyl chloridocarbonate (157 mg, 0.777 mmol, available from Fluka) and stirred under nitrogen. Cyclobutanol (0.082 mL, 1.059 mmol) was added after 1.75 hours. The reaction was allowed to stir under nitrogen for 17 hours. The reaction was partitioned between distilled water (20 mL) and EtOAc (60 mL). The aqueous layer was extracted with EtOAc (60 mL) and the organic fractions were combined, washed (brine (50 mL)), dried (sodium sulfate) and evaporated to dryness to give a yellow solid (346 mg). The residue was purified by SP4 on a 25+M Biotage silica column, eluting with a gradient of 0 to 50% ethyl acetate in cyclohexane. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (39 mg). LCMS (Method C): Rt=1.05, MH+=383

Workup

  1. stirringto stir under nitrogen for 17 hours
  2. customThe reaction was partitioned
  3. distillationbetween distilled water (20 mL) and EtOAc (60 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (60 mL)
  5. washwashed (brine (50 mL))
  6. dry with materialdried (sodium sulfate)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9c81e526f82546efa795eb8bd85f10a6
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…