3-Aminoquinoline → HCID 10406058, compound

HRID 1944534Notes

Reaction equation

HRID 1944534 reaction equation
[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([OH:17])=O)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[N:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[C:44]([NH2:52])[CH:43]=1>C(#N)C>[N:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[C:44]([NH:52][C:15]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:7]=[CH:8]3)=[O:17])[CH:43]=1

Participants

5

Reactant 3

HCID 113753-AminoquinolineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 63748402HCID 63748402, compound

Product 1

HCID 10406058HCID 10406058, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-pentyl-1H-indole-5-carboxylic acid (0.687, 2.97 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophospate (HBTU) (1.18 g, 3.11 mmol) and N,N-diisopropylethyl (1.14 mL, 6.53 mmol) in acetonitrile (20 mL) was stirred at ambient temperature for 5 minutes. Quinolin-3-ylamine (1.93 g, 13.4 mmol) was added, and the solution was heated at reflux for 18 hours. The solvent was evaporated in vacuo, and the residue was partitioned between dichloromethane and water. The product was preabsorbed onto silica gel and purified by flash chromatography using ethyl acetate in hexane as the eluant, to give the product, 0.40 g (38%). MS: m/z 358 (MH+). 1H NMR (DMSO-d6): 0.84 (t, 3 H), 1.23-1.34 (m, 4 H), 1.73-1.83 (m, 2 H), 4.24 (t, 2 H), 6.64 (d, 1 H), 7.53 (d, 1 H), 7.56-7.69 (m, 3 H), 7.86 (d, 1 H), 7.98 (t, 2 H), 8.37 (s, 1 H), 8.89 (d, 1 H), 9.21 (d, 1 H) and 10.60 (s, 1 H).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was partitioned between dichloromethane and water
  5. customThe product was preabsorbed onto silica gel
  6. custompurified by flash chromatography
  7. customto give the product, 0.40 g (38%)

Sources & evidence

ORD record
ord-7befbf71c5414352a19c91c6372c3a84
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

Loading…