Toluene → 1-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

HRID 2366927Notes

Reaction equation

HRID 2366927 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.Cl[C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28].C1(C)C=CC=CC=1>ClCCl>[CH3:31][CH:30]([O:29][C:27](=[O:28])[NH:15][C@H:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)[N:4]([C:1](=[O:3])[CH3:2])[C@@H:5]([CH3:16])[CH2:6]1)[CH3:32]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 67194540cis-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine

Product 1

HCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

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) (3.165 g, 9.90 mmol) and DIPEA (5.19 ml, 29.7 mmol) were stirred in dichloromethane (DCM) (66.0 ml) under nitrogen. 1M isopropyl chloroformate in toluene (14.85 ml, 14.85 mmol) was added, the mixture stirred for 2 hours, evaporated to dryness, partitioned between ethyl acetate (200 ml) water (70 ml) and the aqueous layer run off. The organic layer was washed (water (50 ml), brine (20 ml)), dried (sodium sulfate), evaporated to dryness, loaded on to a 40+M Biotage silica column and eluted with cyclohexane:ethyl acetate (9:1 to 1:1). The product containing fractions were evaporated to a white solid (3.23 g). LCMS (Method B): Rt=1.03, MH+=371

Workup

  1. customevaporated to dryness
  2. custompartitioned between ethyl acetate (200 ml) water (70 ml)
  3. washThe organic layer was washed (water (50 ml), brine (20 ml))
  4. dry with materialdried (sodium sulfate)
  5. customevaporated to dryness
  6. washeluted with cyclohexane:ethyl acetate (9:1 to 1:1)
  7. additionThe product containing fractions
  8. customwere evaporated to a white solid (3.23 g)

Sources & evidence

ORD record
ord-b994f6baa11a49eeaf82eddfdbd67848
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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