Pyridine → HCID 68519721, compound

HRID 1171039Notes

Reaction equation

HRID 1171039 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[O:10][N:9]=2)=[CH:4][CH:3]=1.[N:18]1C=CC=CC=1.[CH3:24][C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>CN(C=O)C>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:31]([C:27]4[CH:28]=[CH:29][CH:30]=[C:25]([CH3:24])[CH:26]=4)[C:32]([NH2:18])=[O:33])=[CH:3][CH:4]=3)[C:16]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 69303m-Tolyl isocyanateHCID 10036673HCID 10036673, compound

Product 1

HCID 68519721HCID 68519721, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. solution of Example 30 (126 mg, 0.3 mmol) in DMF (2 mL) at room temperature was treated with pyridine (0.121 mL, 1.5 mmol) and 3-methylphenylisocyanate (0.038 mL, 0.3 mmol) and stirred overnight. The reaction mixture was poured into ice water and filtered. The filter cake was recrystallized from ethyl acetate/hexanes to provide 87 mg (80% yield) of the desired product. MS (ESI(+)) m/e 361 (M+H)+; 1H NMR (DMSO-d6) δ 9.00 (s, 1H), 8.69 (s, 1H), 8.42 (s, 1H), 7.68 (q, J=15, 8.7 Hz, 4H), 7.10-7.40 (m, 3H), 6.82 (d, J=7.2 Hz, 1H), 2.28 (s, 3H).

Workup

  1. filtrationfiltered
  2. customThe filter cake was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d399adee91ab48f6a2e151144df23873
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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