3-Aminoquinoline → HCID 29330391, compound

HRID 1944529Notes

Reaction equation

HRID 1944529 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[N:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[C:37]([NH2:45])[CH:36]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:45][C:37]2[CH:36]=[N:35][C:44]3[C:39]([CH:38]=2)=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:8])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 113753-AminoquinolineHCID 792226-Chloronicotinic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 29330391HCID 29330391, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-chloro-nicotinic acid (2.95 g, 18.7 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophospate (HBTU) (7.09 g, 18.7 mmol), quinolin-3-ylamine (2.7 g, 18.7 mmol), and N,N-diisopropylethylamine (8.2 mL, 46.7 mmol) in acetonitrile was heated at reflux. The resultant mixture was cooled, and the crystalline product was collected by filtration, to give a colorless solid, 3.1 g (58%). MS: m/z 284 (MH+). 1H NMR (DMSO-d6): 7.61 (t, 1 H), 7.70 (d of t, 1 H), 7.77, (d, 1 H), 8.00 (d, 2 H), 8.43 (d of d, 1 H), 8.85 (d, 1 H), 9.05 (d, 1 H), 9.14 (d, 1 H) and 10.95 (s, 1 H).

Workup

  1. temperatureat reflux
  2. filtrationthe crystalline product was collected by filtration
  3. customto give a colorless solid, 3.1 g (58%)

Sources & evidence

ORD record
ord-6cb7022d26ac46608bf89224c76d8e60
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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