3-Aminoquinoline → HCID 66815771, compound

HRID 1944544Notes

Reaction equation

HRID 1944544 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=O)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:53][C:54]1[CH:55]=[N:56][C:57]2[C:62]([CH:63]=1)=[CH:61][CH:60]=[CH:59][CH:58]=2>C(#N)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[O:19])[NH:53][C:54]3[CH:55]=[N:56][C:57]4[C:62]([CH:63]=3)=[CH:61][CH:60]=[CH:59][CH:58]=4)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 113753-AminoquinolineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 98784151-[(TERT-BUTOXY)CARBONYL]-2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID

Product 1

HCID 66815771HCID 66815771, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,3-dihydro-indole-1,5-dicarboxylic acid 1-tert-butyl ester (1.5 g, 5.70 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (2.37 g, 6.27 mmol), N,N-diisopropylethylamine (2.41 mL, 13.8 mmol) and 3-aminoquinoline (0.904 g, 6.27 mmol) in acetonitrile was heated to reflux for 20 hours. The solvent was evaporated in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was separated, and the solvent was evaporated. The residue was purified by flash chromatography on silica gel eluted with ethyl acetate/hexane to give the product, 1.43 g (64%). MS: m/z 390 (MH+). 1H NMR (DMSO-d6): δ 1.54 (s, 9 H), 3.16 (t, 2 H), 4.00 (t, 2 H), 7.57-7.83 (m, 3 H), 7.88-8.00 (m, 4 H), 8.84 (d, 1 H), 9.15 (d, 1 H) and 10.53 (s, 1 H).

Workup

  1. temperatureto reflux for 20 hours
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between water and dichloromethane
  4. customThe organic layer was separated
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluted with ethyl acetate/hexane
  8. customto give the product, 1.43 g (64%)

Sources & evidence

ORD record
ord-fe04bb354641433693dc1fc2f81d29ff
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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