1-Heptanol, 7-bromo- → N-[1-({2-Chloro-4-[(7-hydroxyheptyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide

HRID 1946372Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[N:11]1.CC(C)([O-])C.[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][OH:40]>C(#N)C.CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][OH:40])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:18]([F:24])=[CH:19][CH:20]=[CH:21][C:22]=2[F:23])=[N:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-{1-[(2-chloro-4-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide (for a preparation see Example 31)(30 mg, 0.082 mmol) in acetonitrile (0.5 ml) was added potassium t-butoxide (9.4 mg, 0.084 mmol) and then 7-bromo-1-heptanol (0.015 ml, 0.099 mmol, Aldrich). The reaction vessel was sealed and heated in a Biotage Initiator microwave to 100° C. for 15 min. After cooling the reaction was diluted with DMSO (0.5 ml) and purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as a colourless gum (6.7 mg);

Workup

customThe reaction vessel was sealed
temperatureAfter cooling the reaction
custompurified by MDAP on Sunfire C18 column
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-115d4f7805dc4d5badd51f599480d2ab
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399436B2

Reaction notes

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