Water → HCID 178424891, compound

HRID 892211Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11]N1C=C(CO)N=C1.[H-].[Na+].Br[CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:24]=1[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26].[OH2:37].C[N:39]1[C:44](=O)[N:43](C)[CH2:42][CH2:41][CH2:40]1>C1COCC1>[CH3:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:23]([CH:22]([O:37][CH2:40][C:41]2[N:39]=[CH:44][NH:43][CH:42]=2)[CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[C:24]=1[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

(1-Quinolin-2-ylmethyl-1H-imidazol-4-yl)-methanol (350 mg, 1.46 mmol, example 87) is dissolved in 20% DMPU in THF (5 mL) and cooled to 0° C. Sodium hydride (60%, 60 mg, 1.50 mmol) is added portionwise, and the contents stirred for 15 min. Isobutyl 2-bromomethyl-6-methyl-benzoate (57%, 730 mg, 1.46 mmol, example 2) is added, the reaction is allowed to come to r.t. and stirred overnight. The contents are poured into water (200 mL) and extracted with dichloromethane (3×75 mL). The organic fractions are pooled and washed with brine (3×100 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material is purified by flash chromatography (silica, 3% methanol in dichloromethane) to give the title compound. MS (ESI) 443 (M+H)+.

Workup

customto come to r.t.
stirringstirred overnight
extractionextracted with dichloromethane (3×75 mL)
washwashed with brine (3×100 mL)
dry with materialdried over MgSO4
filtrationfiltered
customThe crude material is purified by flash chromatography (silica, 3% methanol in dichloromethane)

Sources & evidence

ORD record: ord-2f6a5792f3604916bab104cd8b2c9605
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005440B1

Reaction notes

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