Pyridine → HCID 57330623, compound

HRID 1754350Notes

Reaction equation

HRID 1754350 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[N:13]=[CH:14][C:15]([C:18]2[CH:19]=[C:20]([C:25]3[C:29](=[O:30])[C:28]([CH3:32])([CH3:31])[O:27][N:26]=3)[CH:21]=[CH:22][C:23]=2[CH3:24])=[N:16][CH:17]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[CH:17]=[N:16][C:15]([C:18]2[CH:19]=[C:20]([C:25]3[C:29](=[O:30])[C:28]([CH3:31])([CH3:32])[O:27][N:26]=3)[CH:21]=[CH:22][C:23]=2[CH3:24])=[CH:14][N:13]=1)=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 691102-Chlorobenzoyl chlorideHCID 67515975HCID 67515975, compound

Product 1

HCID 57330623HCID 57330623, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a 0° C. cooled and stirred, solution of 2-chlorobenzoyl chloride (43 μL, 0.34 mmol, 1.0 eq) in DCM (2 mL) was added drop wise a solution of Intermediate 1b, (100 mg, 0.34 mmol, 1.0 eq) in DCM (5 mL) followed by pyridine (47 μL, 0.44 mmol, 1.3 eq). The resulting mixture was stirred at room temperature for 15 h. The reaction was diluted with DCM (10 mL), and washed with 10% hydrochloric acid (5 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum and the crude product was purified by flash column chromatography (silica gel, ethyl acetate in hexane as eluent) to afford 50 mg of the title product as a white solid. 1HNMR (400 MHz, CDCl3) δ 9.78 (s, 1H), 8.80 (s, 1H, D2O exchangeable), 8.39 (s, 1H), 8.19 (d, J=2.0 Hz, 1H), 8.09 (dd, J=8.0, 2.0 Hz, 1H), 7.84 (dd, J=7.0, 1.5 Hz, 1H), 7.52-7.40 (m, 4H), 2.47 (s, 3H), 1.48 (s, 6H); ESI-MS (m/z) 435, 437 [(MH)+, Cl35,37].

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 15 h
  2. washwashed with 10% hydrochloric acid (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. customthe crude product was purified by flash column chromatography (silica gel, ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-d430cb2f7753444a97104e1233c86024
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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