8-Aminoquinoline → HCID 41661718, compound

HRID 525315Notes

Reaction equation

HRID 525315 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][C:52]=2[NH2:54])[CH:47]=[CH:46][CH:45]=1>CN(C=O)C.C([O-])(O)=O.[Na+].O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:54][C:52]2[CH:51]=[CH:50][CH:49]=[C:48]3[C:53]=2[N:44]=[CH:45][CH:46]=[CH:47]3)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 113598-AminoquinolineHCID 120854-Iodobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 41661718HCID 41661718, compoundYield 64.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-iodobenzoic acid (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (9.26 g, 37.3 mmol), DIEA (13.05 mL, 74.7 mmol), HATU (7.10 g, 18.67 mmol) and quinolin-8-amine (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (7 g, 48.6 mmol) in DMF (124 mL) was stirred under nitrogen overnight at room temperature. The reaction mixture was diluted with saturated NaHCO3 (100 mL) and water (300 mL) yielding a yellow/brown precipitate which was filtered, washed with water (100 mL) and dried on high vacuum to obtain 4-iodo-N-(quinolin-8-yl)benzamide (9 g, 24.05 mmol, 64.4% yield) as a yellow brown solid. 1H NMR (400 MHz, DMSO-d6) δ=10.65 (s, 1H), 8.98 (dd, J=1.6, 4.3 Hz, 1H), 8.70 (dd, J=1.4, 7.6 Hz, 1H), 8.47 (dd, J=1.7, 8.3 Hz, 1H), 8.03-7.98 (m, 2H), 7.83-7.79 (m, 2H), 7.76 (dd, J=1.3, 8.2 Hz, 1H), 7.71-7.62 (m, 2H).

Workup

  1. customyielding a yellow/brown precipitate which
  2. filtrationwas filtered
  3. washwashed with water (100 mL)
  4. customdried on high vacuum

Sources & evidence

ORD record
ord-957cf08df4d64ff0a7c588451fc73a5f
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…