Triethylamine → HCID 10449843, compound

HRID 1672344Notes

Reaction equation

HRID 1672344 reaction equation
[C-]#N.[K+].[CH2:4]([N:6](CC)CC)C.[Cl:11][C:12]1[CH:21]=[CH:20][C:19]2[N+:18]([O-])=[CH:17][C:16]3[N:23]=[CH:24][N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:32])[C:15]=3[C:14]=2[CH:13]=1>CN(C=O)C.C[Si](C)(C)Cl>[Cl:11][C:12]1[CH:21]=[CH:20][C:19]2[N:18]=[C:17]([C:4]#[N:6])[C:16]3[N:23]=[CH:24][N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:32])[C:15]=3[C:14]=2[CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 10359250HCID 10359250, compound

Product 1

HCID 10449843HCID 10449843, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6397ChlorotrimethylsilaneSolvent

Conditions

Temperature
105 °C

Procedure

38.1 mg (0.5679 mmol) potassium cyanide and 239 μl (1.704 mmol) triethylamine (dry; Fluka) in 6 ml dry DMF, 182 μl trimethylchlorosilane (Fluka) are added within 10 min to a solution of 100 mg (0.30 mmol) of 8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline 5-oxide (Example 71). The reaction mixture is stirred for 48 h at ca. 100-110° C. bath temperature. The cold solution is filtered, the solvent is evaporated. The residue is purified by chromatography on silica gel (CH2Cl2-methanol 9:1). The compound can be crystallized from CH2Cl2-hexane. mp: 248-250° C.; MS: 339 (M++1); HPLC: tret=13.19 min (Grad 1).

Workup

  1. filtrationThe cold solution is filtered
  2. customthe solvent is evaporated
  3. customThe residue is purified by chromatography on silica gel (CH2Cl2-methanol 9:1)
  4. customThe compound can be crystallized from CH2Cl2-hexane
  5. customtret=13.19 min (Grad 1)

Sources & evidence

ORD record
ord-939e6ffb0eaa45a09803e6cd3a743603
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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