Picolinic acid → {4-[6-(4-Methanesulfonyl-phenylamino)-5-nitro-pyrimidin-4-yloxy]-piperidin-1-yl}-pyridin-2-yl-methanone
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](Cl)=[O:35].N1C=CC=CC=1C(O)=O.O=S(Cl)Cl>CN(C=O)C.C(N(CC)CC)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[CH:14][N:15]=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][N:25]([C:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=4)=[O:35])[CH2:24][CH2:23]3)[C:17]=2[N+:18]([O-:20])=[O:19])=[CH:7][CH:6]=1)(=[O:4])=[O:3]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Compound A26 was prepared in a similar manner as described above using (4-methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine (i.e., Compound A2) (16 mg, 0.037 mmol), triethylamine (50 μl), pyridine-2-carbonyl chloride (10 mg, 0.046 mmol) [Pyridine-2-carbonyl chloride was prepared by refluxing picolinic acid with SOCl2 for 3 hours and worked up in general method], DMF (1 mL), 1H NMR (CDCl3, 400 MHz) δ 1.95 (m, 2H), 2.13 (m, 2H), 3.07 (s, 3H), 3.65 (m, 2H), 3.79 (m, 2H), 4.13 (m, 1H), 5.72 (m, 1H), 7.37 (m, 1H), 7.67 (m, 1H), 7.81 (m, 1H), 7.87 (d, 2H), 7.97 (d, 2H), 8.41 (s, 1H), 8.60 (m, 2H), 10.19 (s, 1H). Exact mass calculated for C22H22N6O6S 498.13, found 499.3 (MH+).
Workup
- customCompound A26 was prepared in a similar manner
- customwas prepared
Sources & evidence
- ORD record
- ord-3e3360e3be914376ac2a862875951970
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838525B2
Reaction notes
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