1,1'-Carbonyldiimidazole → HCID 10251391, compound

HRID 658493Notes

Reaction equation

HRID 658493 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[C:19]([N:26]1[CH:30]=[CH:29]N=C1)(N1C=CN=C1)=[O:20].[CH3:31][N:32]1[C:40]2[C:35](=[CH:36]C(N)=C[CH:39]=2)[CH:34]=[N:33]1>C(Cl)Cl>[CH3:31][N:32]1[C:40]2[C:35](=[CH:36][C:30]([NH:26][C:19]([NH:18][C:14]3[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=3)[O:11][C:9]3[CH:8]=[CH:7][N:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=3)=[O:20])=[CH:29][CH:39]=2)[CH:34]=[N:33]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27680321-methyl-1H-indazol-5-amineHCID 60125954HCID 60125954, compound

Product 1

HCID 10251391HCID 10251391, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(3-amino-phenoxy)-pyridine-2-carboxylic acid methyl ester (0.79 g, 5.35 mmol) in CH2Cl2 (3 mL) was added 1,1′-carbonyldiimidazole (0.87 g, 5.35 mmol), and the reaction mixture was stirred at room temperature for 12 h. A solution of 1-methyl-5-aminoindazol (1.02 g, 6.96 mmol) in CH2Cl2 (4 mL) was added, and the mixture stirred at room temperature an additional 8 h. The mixture was concentrated in vacuo. Purification of the crude product by column chromatography eluted with CH2Cl2/MeOH (95:5) gave 850 mg (38%) of the title compound. 1H-NMR (CD3OD) δ 8.57 (dd, 1H), 7.95 (d, 1H), 7.87 (d, 1H), 7.54 (d, 1H), 7.53-7.51 (m, 2H), 7.47-7.32 (m, 2H), 7.32 (d, 1H), 7.21 (dd, 1H), 6.86 (dd, 1H). 4.07 (s, 3H), 3.96 (s, 3H); MS LC-MS [M+H]+=418.2, RT=2.91 min.

Workup

  1. stirringthe mixture stirred at room temperature an additional 8 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customPurification of the crude product by column chromatography
  4. washeluted with CH2Cl2/MeOH (95:5)

Sources & evidence

ORD record
ord-df1478ed5dd54d3b9eff80302cc09004
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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