1-Iodopropane → HCID 57785899, compound

HRID 1399188Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:16]=[CH:17][C:18]([OH:22])=[N:19][C:20]=4[CH3:21])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([O:28][CH:29]([F:31])[F:30])[C:24]([F:27])([F:26])[F:25])=[CH:4][CH:3]=1.I[CH2:33][CH2:34][CH3:35]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:20]([CH3:21])=[N:19][C:18]([O:22][CH2:33][CH2:34][CH3:35])=[CH:17][CH:16]=4)[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([O:28][CH:29]([F:30])[F:31])[C:24]([F:27])([F:26])[F:25])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-{9-chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl}-6-methylpyridin-2-ol (65.3 mg, 0.141 mmol) in toluene (1.5 mL) was added silver carbonate (77.8 mg, 0.282 mmol) and 1-iodopropane (68.8 μL, 0.705 mmol). The reaction mixture was stirred at 50° C. for 13 hrs. After cooling the mixture was filtered through on the pad of celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography eluting with a 0-40% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless powder (52.5 mg, 0.104 mmol, 74%).

Workup

temperatureAfter cooling the mixture
filtrationwas filtered through on the pad of celite
concentrationThe filtrate was concentrated
customThe residue was purified by silica gel column chromatography
washeluting with a 0-40% ethyl acetate/n-hexane gradient mixture
customThe resulting solid was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-5033e8a3a1dd47cba82b241903670357
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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