Dimethylamine → HCID 68816267, compound

HRID 735486Notes

Reaction equation

[CH2:1]([N:8]1[C:16]([C:17]2[CH:33]=[CH:32][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([O:27]C)=O)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:34]([F:37])([F:36])[F:35])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[CH3:41][NH:42][CH3:43]>CO>[CH2:1]([N:8]1[C:16]([C:17]2[CH:33]=[CH:32][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([N:42]([CH3:43])[CH3:41])=[O:27])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:34]([F:36])([F:35])[F:37])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

This compound was prepared from Example 912. Methyl 3-{4-[2-benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}benzoate (49 mg, 0.0971 mmol) was dissolved in a 2M solution of dimethylamine in methanol (1.5 mL), 0.5 mg of sodium cyanide was added and the reaction mixture was stirred at 60° C. overnight. The solvent was evaporated, the residue 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 9 mg of analytically pure product.

Workup

customThis compound was prepared from Example 912
additionwas added
customThe solvent was evaporated
dissolutionthe residue dissolved in CH2Cl2
washwashed with brine
customThe combined organic phases were dried
customevaporated
customthe crude material was purified by HPLC
customto afford 9 mg of analytically pure product

Sources & evidence

ORD record: ord-86629805f4134a63aebd5a30196dfd18
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592363B2

Reaction notes

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