2-Chloroquinoline → HCID 86588662, compound

HRID 857061Notes

Reaction equation

HRID 857061 reaction equation
[F:1][C:2]1[C:3]2[CH:4]3[CH2:13][CH:8]([C:9]=2[CH:10]=[CH:11][CH:12]=1)[CH2:7][N:6](C(=O)C(F)(F)F)[CH2:5]3.[Cl:20][C:21]1[CH:30]=[CH:29]C2C(=CC=CC=2)[N:22]=1>>[ClH:20].[Cl:20][C:21]1[CH:30]=[CH:29][C:12]2[C:11](=[CH:10][C:9]3[CH:8]4[CH2:13][CH:4]([C:3]=3[C:2]=2[F:1])[CH2:5][NH:6][CH2:7]4)[N:22]=1

Participants

3

Reactant 2

HCID 119282-ChloroquinolineHCID 21864703HCID 21864703, compound

Product 1

HCID 86588662HCID 86588662, compound

Procedure

1-(6-Chloro-10-fluoro-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-yl)-2,2,2-trifluoro-ethanone 3-Fluoro-10-aza-tricyclo[6.3.1.02,7]-dodeca-2(7),3,5-triene was converted to 1-(3-Fluoro-10-aza-tricyclo[6.3.1.02,7]-dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone by the methods described in Example 7A. This product was nitrated as described in Example 7B. The resulting mixture of nitrated products was reduced as described in Example 8, then converted to a chloroquinoline as described in Examples 54 and 55. These products were separated by column chromatography on silica gel to provide the title compound. (TLC: 50% ethyl acetate/hexanes, Rf 0.50).

Workup

  1. additionThe resulting mixture of nitrated products
  2. customThese products were separated by column chromatography on silica gel

Sources & evidence

ORD record
ord-b89decee575649008455a485d735eb9a
Source dataset
uspto-grants-2006_12
Patent number
US07144882B2

Reaction notes

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