Pyridine → HCID 67187050, compound

HRID 551831Notes

Reaction equation

[F:1][C:2]1([F:14])[C:4]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH2:6][CH2:5]2)[CH2:3]1.N1C=CC=CC=1.[C:21](Cl)(Cl)=[O:22].Cl.Cl.[NH:27]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:33]=[N:34][NH:35][CH:36]=2)[CH2:28]1>C1(C)C=CC=CC=1.C(N(CC)CC)C.ClCCl>[F:14][C:2]1([F:1])[C:4]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([C:21]([N:27]3[CH2:31][CH2:30][CH:29]([C:32]4[CH:33]=[N:34][NH:35][CH:36]=4)[CH2:28]3)=[O:22])[CH2:6][CH2:5]2)[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

0.071 g of 2,2-difluoro-2′,3′-dihydro-1′H-spiro[cyclopropane-1,4′-quinoline], 0.03 ml of pyridine and 8.4 ml of dichloromethane are placed in a 50 ml round-bottomed flask under a nitrogen atmosphere. 0.17 ml of a 20% solution of phosgene in toluene is added at 0° C. and then the reaction mixture is left stirring at 0° C. for ½ hour and at ambient temperature for one hour. 0.05 ml of triethylamine and 0.044 g of 4-(pyrrolidin-3-yl)-1H-pyrazole dihydrochloride are subsequently added at 0° C. and the reaction mixture is stirred for eighteen hours and then concentrated under reduced pressure. The residue is chromatographed on silica gel eluted with a 5% mixture of methanol in dichloromethane. 0.038 g of 2,2-difluoro-1′-{[3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]carbonyl}-2′,3′-dihydro-1′H-spiro[cyclopropane-1,4′-quinoline] is obtained.

Workup

waitthe reaction mixture is left
stirringthe reaction mixture is stirred for eighteen hours
concentrationconcentrated under reduced pressure
customThe residue is chromatographed on silica gel
washeluted with a 5% mixture of methanol in dichloromethane

Sources & evidence

ORD record: ord-0699b5090b934bee9016c747fd272f5e
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947834B2

Reaction notes

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