Ammonia → HCID 68820477, compound

HRID 735487Notes

Reaction equation

[CH2:1]([N:8]1[C:16]([C:17]2[CH:32]=[CH:31][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=O)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:33]([F:36])([F:35])[F:34])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:37]>O1CCOCC1>[CH2:1]([N:8]1[C:16]([C:17]2[CH:32]=[CH:31][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([NH2:37])=[O:27])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:33]([F:34])([F:36])[F:35])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

3-{4-[2-benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}benzoic acid (39 mg, 0.08 mmol) in 0.8 mL dioxane was added to NbCl5 (64 mg, 0.238 mmol), followed by 0.95 mL NH3 (0.5M in dioxane). The temperature was slowly raised to 50° C. and stirred for 2 days. The solvents were evaporated and the residue dissolved in CH2Cl2, followed by filtration of the precipitate. The residue was dissolved in CH2Cl2 and washed with brine. The combined organic phases were dried, evaporated and the crude material was purified by HPLC using a gradient with an acidic mobile phase on an ACE-C8 column to afford analytically pure product.

Workup

customThe solvents were evaporated
dissolutionthe residue dissolved in CH2Cl2
filtrationfollowed by filtration of the precipitate
dissolutionThe residue was dissolved in CH2Cl2
washwashed with brine
customThe combined organic phases were dried
customevaporated
customthe crude material was purified by HPLC
customto afford analytically pure product

Sources & evidence

ORD record: ord-330d96539e1c4e588b0f8c0acd977feb
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592363B2

Reaction notes

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