3-Aminoquinoline → HCID 66815452, compound

HRID 1944520Notes

Reaction equation

HRID 1944520 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]([NH2:37])[CH:28]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(#N)C>[C:10]([O:14][C:15](=[O:16])[NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22](=[O:24])[NH:37][C:29]2[CH:28]=[N:27][C:36]3[C:31]([CH:30]=2)=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:25][CH:26]=1)([CH3:11])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 113753-AminoquinolineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acid

Product 1

HCID 66815452HCID 66815452, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-diisopropylethyl amine (12.1 mL, 69.4 mmol) was added to a solution of 4-tert-butoxycarbonylamino-benzoic acid (9.05 g, 38.1 mmol), quinolin-3-ylamine (5.0 g, 34.7 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophospate (HBTU) (14.5 g, 38.1 mmol) in acetonitrile (200 mL) and was stirred at ambient temperature for ten minutes. The solution was heated at reflux for approximately 18 hours. Upon cooling to room temperature, the product crystallized and was collected by filtration, to give a colorless solid, 7.9 g (63%). MS: m/z 364 (MH+). 1H NMR (DMSO-d6): δ 1.51 (s, 9 H), 7.57-7.70 (m, 4 H), 7.75-8.00 (m, 4 H), 8.83 (d, J=2 Hz, 1 H), 9.15 (d, J=2 Hz, 1 H), 9.75 (br s, 1 H) and 10.54 (br s, 1 H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureUpon cooling to room temperature
  4. customthe product crystallized
  5. filtrationwas collected by filtration
  6. customto give a colorless solid, 7.9 g (63%)

Sources & evidence

ORD record
ord-c70cd06eaebf42ba899ae5057bd7efa7
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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