Picolinic acid → HCID 22282035, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C(O)=O.C([N:12]([CH2:15]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.[C:34]([C:38]1[CH:43]=[CH:42][C:41]([S:44]([NH:47][C:48]2[N:52]([CH3:53])[N:51]=[C:50]([O:54][CH2:55][CH2:56][OH:57])[C:49]=2[C:58]2[CH:63]=[CH:62][C:61]([CH3:64])=[CH:60][CH:59]=2)(=[O:46])=[O:45])=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:34]([C:38]1[CH:39]=[CH:40][C:41]([S:44]([NH:47][C:48]2[N:52]([CH3:53])[N:51]=[C:50]([O:54][CH2:55][CH2:56][O:57][C:15](=[O:24])[NH:12][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:49]=2[C:58]2[CH:63]=[CH:62][C:61]([CH3:64])=[CH:60][CH:59]=2)(=[O:45])=[O:46])=[CH:42][CH:43]=1)([CH3:37])([CH3:36])[CH3:35]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 37.5 °C
Procedure
2-Pyridine carboxylic acid (278 mg) and triethylamine (0.321 ml) in toluene (10 ml) was stirred under nitrogen at room temperature for 10 mins. Diphenyl phosphoryl azide (621 mg) was added to the reaction and warmed to 35-40° C. for 1 hour and then at 100° C. until the effervescence had ceased. 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (200 mg) (Example 2) and 4-dimethylaminopyridine (8 mg) in toluene (5 ml) was added to the reaction and stirred at 100° C. for a further 45 minutes. The reaction was quenched with water (2 ml) and left to cool. The crude product was loaded onto silica (25 g) and eluted with a solvent gradient of pentane:ethyl acetate (1:0 to 0:1) to yield the title compound as a white solid (106 mg).
Workup
- customat 100° C.
- customThe reaction was quenched with water (2 ml)
- waitleft
- temperatureto cool
- washeluted with a solvent gradient of pentane:ethyl acetate (1:0 to 0:1)
Sources & evidence
- ORD record
- ord-dcdd9df6b4104cba832506f0b894e22c
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06962923B2
Reaction notes
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