HCID 10405339, compound → HCID 10427957, compound

HRID 1672338Notes

Reaction equation

HRID 1672338 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[N:13]=[CH:12][C:11]4[N:17]=[CH:18][N:19]([C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[C:22]#[N:23])[C:10]=4[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.N.CO.C(O)C.[Ni]>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[N:13]=[CH:12][C:11]4[N:17]=[CH:18][N:19]([C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[CH2:22][NH2:23])[C:10]=4[C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 1

HCID 10405339HCID 10405339, compound

Product 1

HCID 10427957HCID 10427957, compound

Reagents, catalysts & solvents 5

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 100 mg of (0.288 mmol) 2-(8-phenyl-imidazo[4,5-c]quinolin-1-yl)-benzonitrile (Example 63) in 2 ml THF and 6 ml 10% ammonia in methanol are added ca. 50 mg Raney-Ni in ethanol. The solution is hydrogenated at rt for 6 h. The catalyst is filtered off and the raw material is purified by chromatography on silica gel (CH2Cl2-methanol 9:1) and crystallization (ethyl-acetate-hexane). mp: 163-1650° C.; MS: 351 (M++1); HPLC: tret=6.42 min (Grad 1).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe raw material is purified by chromatography on silica gel (CH2Cl2-methanol 9:1) and crystallization (ethyl-acetate-hexane)
  3. customtret=6.42 min (Grad 1)

Sources & evidence

ORD record
ord-61e322b30f244ab692a781309b67a0d1
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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