Pyridine → HCID 86673817, compound

HRID 1052100Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:18]([OH:20])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][NH:22][O:23][CH3:24].N1C=CC=CC=1.CCN=C=NCCCN(C)C.Cl>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:18]([N:22]([O:23][CH3:24])[CH3:21])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The title compound was prepared in a similar manner as described by F. Crestey et al., Tetrahedron 2007, 63, 419-428. To 5-(benzyloxy)-1H-indazole-3-carboxylic acid [177941-16-1](3.50 g, 13.1 mmol) in THF (70 mL) was added N,O-dimethylhydroxylamine (1.40 g, 14.4 mmol). The mixture was cooled to 0° C. before the addition of pyridine (2.30 mL, 28.7 mmol). The solution was stirred at 0° C. for 1.5 h, and then at RT for 1 h. Pyridine (2.10 mL, 26.1 mmol) and EDCl (5.00 g, 26.1 mmol) were added and the mixture was stirred at RT overnight. Water was added to the reaction mixture followed by extraction (×3) with CH2Cl2. The combined organics were washed with saturated aqueous NaHCO3 solution, dried (Phase separator) and concentrated to give the title compound. MS (LC/MS): 312.0 [M+H]+, 334.0 [M+Na]+, 645.1 [2M+Na]+, 310.0 [M−H]−; tR (HPLC conditions e): 4.44 min.

Workup

customThe title compound was prepared in a similar manner
waitat RT for 1 h
stirringthe mixture was stirred at RT overnight
extractionfollowed by extraction (×3) with CH2Cl2
washThe combined organics were washed with saturated aqueous NaHCO3 solution
customdried (Phase separator)
concentrationconcentrated

Sources & evidence

ORD record: ord-25d6f42a509046b19a474c037be7e303
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388199B2

Reaction notes

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