Pyridine → HCID 11303033, compound

HRID 736393Notes

Reaction equation

HRID 736393 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:21]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C1C=CN=CC=1)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:12][C:11]2[CH:13]=[CH:14][C:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)=[CH:9][CH:10]=2)=[O:30])=[CH:32][CH:33]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 3

HCID 1049PyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 221704504-(3-Chloro-2-pyridinyl)aniline

Product 1

HCID 11303033HCID 11303033, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The product from Example 41A (17.5 mg, 0.0855 mmol), DMAP (catalytic amount), and pyridine (21 μL, 0.26 mmol) were combined in CH2Cl2 (0.5 mL) and treated with 4-tert-butylbenzoyl chloride (33 μL, 0.17 mmol). After stirring for 1 hour, the mixture was diluted with saturated NaHCO3 (1 mL) and extracted with CH2Cl2 (3×1 mL). The organic layer was dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (50% diethyl ether in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.59 (dd, 1H), 7.91 (br s, 1H), 7.83 (d, 2H), 7.81 (dd, 1H), 7.78 (d, 4H), 7.51 (d, 2H), 7.21 (dd, 1H), 1.36 (s, 9H); MS (m/z) 365.

Workup

  1. extractionextracted with CH2Cl2 (3×1 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (50% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-bf1f0e805cc947bfa13b439e88aff27e
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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