Pyridine → N-(4-tert-butylphenyl)-4-{3-[(dimethylamino)sulfonyl]-2-pyridinyl}benzamide

HRID 736400Notes

Reaction equation

HRID 736400 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[C:7]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].C(Cl)(C(Cl)=O)=O.N1C=CC=CC=1.[C:34]([C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl.C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.O.CN(C=O)C>[C:34]([C:38]1[CH:39]=[CH:40][C:41]([NH:42][C:16](=[O:18])[C:15]2[CH:14]=[CH:13][C:12]([C:7]3[C:6]([S:3]([N:2]([CH3:1])[CH3:21])(=[O:4])=[O:5])=[CH:11][CH:10]=[CH:9][N:8]=3)=[CH:20][CH:19]=2)=[CH:43][CH:44]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

10

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 698614-Tert-ButylanilineHCID 688226564-{3-[(Dimethylamino)sulfonyl]-2-pyridinyl}benzoic acid

Product 1

HCID 22170451N-(4-tert-butylphenyl)-4-{3-[(dimethylamino)sulfonyl]-2-pyridinyl}benzamide

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 44B (0.917 g, 2.99 mmol) and DMF (0.03 mL) were combined in CH2Cl2 (9 mL) and treated with (COCl)2 (0.32 mL, 3.7 mL). After stirring for 90 minutes, the mixture was diluted with toluene (2 mL) and concentrated to dryness. The residue was dissolved in CH2Cl2 (9 mL) and treated with pyridine (0.36 mL, 4.5 mmol), DMAP (catalytic amount), and 4-tert-butylaniline (0.57 mL, 3.6 mmol). After stirring for 1 hour, the mixture was diluted with water and extracted with CH2Cl2. The organics were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (75% ethyl acetate in hexanes) to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ 8.84 (dd, 1H), 8.44 (dd, 1H), 7.98 (d, 2H), 7.83 (br s, 1H), 7.72 (d, 2H), 7.58 (d, 2H), 7.51 (dd, 1H), 7.41 (d, 2H), 2.43 (s, 6H), 1.33 (s, 9H); MS (m/z) 438.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in CH2Cl2 (9 mL)
  3. stirringAfter stirring for 1 hour
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-91f4babf68de4c3da2b408a7b89a4e9b
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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