Ammonia → HCID 178464870, compound

HRID 2053954Notes

Reaction equation

[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[NH:6][C:7]([CH:9]([NH:11][C:12](=[O:36])[C:13]3[CH:18]=[CH:17][C:16]([N:19]4[C:23]5[CH2:24][CH2:25][CH2:26][C:22]=5[C:21]([C:27]([O:29]CC)=O)=[N:20]4)=[C:15]([C:32]([F:35])([F:34])[F:33])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1.[NH3:39].Cl>CO>[NH2:39][C:27]([C:21]1[C:22]2[CH2:26][CH2:25][CH2:24][C:23]=2[N:19]([C:16]2[CH:17]=[CH:18][C:13]([C:12]([NH:11][CH:9]([C:7]3[NH:6][C:5]4[CH:37]=[CH:38][C:2]([Cl:1])=[CH:3][C:4]=4[N:8]=3)[CH3:10])=[O:36])=[CH:14][C:15]=2[C:32]([F:35])([F:34])[F:33])[N:20]=1)=[O:29]

Participants

Conditions

Temperature: 65 °C

Procedure

130 mg (0.19 mmol) of rac.-N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-4-[3-(ethoxycarbonyl)-5,6-dihydro-4H-cyclopentapyrazol-1-yl]-3-trifluoromethylbenzamide is dissolved in 5 mL of methanol, combined with 6 mL of concentrated ammonia solution, and stirred for 17 hours at 65° C. in a Schlenk flask. The cooled reaction solution is poured onto ice water, adjusted to pH 7.5 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phases are dried and concentrated by evaporation. The residue is chromatographed on silica gel, eluting with ethyl acetate/ethanol (0%-5%). Yield: 50 mg (51%); Rf value: 0.38 (silica gel; ethyl acetate/ethanol=9:1); C24H20ClF3N6O2 (516.91); mass spectrum: (M−H)−=515/517 (chlorine isotope).

Workup

customThe cooled reaction solution
additionis poured onto ice water
extractionextracted with ethyl acetate
customThe organic phases are dried
concentrationconcentrated by evaporation
customThe residue is chromatographed on silica gel
washeluting with ethyl acetate/ethanol (0%-5%)

Sources & evidence

ORD record: ord-0b3056a4ed0844fd856731fecc1b101a
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326791B2

Reaction notes

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