Water → HCID 57486811, compound

HRID 577773Notes

Reaction equation

[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]([CH2:13][C:14]1[CH:15]=[C:16]2[C:23]([CH3:24])=[N:22][N:21]([CH3:25])[C:17]2=[N:18][C:19]=1[Cl:20])[C:8]1[N:9]=[N:10][NH:11][N:12]=1.[H-].[Na+].[CH3:37]I.O>CN(C=O)C>[F:32][C:29]([F:30])([F:31])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:33])([F:1])[F:34])[CH:28]=1)[CH2:6][N:7]([CH2:13][C:14]1[CH:15]=[C:16]2[C:23]([CH3:24])=[N:22][N:21]([CH3:25])[C:17]2=[N:18][C:19]=1[Cl:20])[C:8]1[N:9]=[N:10][N:11]([CH3:37])[N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of (3,5-bis-trifluoromethyl-benzyl)-(6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-ylmethyl)-(2H-tetrazol-5-yl)-amine (8.5 g, 10 mmol) and sodium hydride (0.81 g, 30 mmol) in DMF (150 mL) was stirred at 0° C. for 20 minutes. Thereafter, methyl iodide (3.5 g, 20 mmol) was added and the resulting mixture was stirred at 0-10° C. for 30 minutes. Water (100 mL) was added to the reaction mixture, which was then extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by column chromatography over 230-400 mesh silica gel. Elution of the column with 10% acetone in hexanes gave the pure product as a colorless solid (6.3 g), yield: 75%.

Workup

stirringthe resulting mixture was stirred at 0-10° C. for 30 minutes
extractionwas then extracted with ethyl acetate (3×100 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography over 230-400 mesh silica gel
washElution of the column with 10% acetone in hexanes

Sources & evidence

ORD record: ord-3c8e79d4645e4ed5a6c04065dae8b304
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040558B2

Reaction notes

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