Ethyl orthoformate → HCID 10356351, compound

HRID 1672311Notes

Reaction equation

HRID 1672311 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([NH2:12])=[C:5]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20].[CH2:21](OC(OCC)OCC)C>>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[CH:21][N:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[F:20])[C:5]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 60046933HCID 60046933, compound

Product 1

HCID 10356351HCID 10356351, compound

Procedure

200 mg (0.74 mmol) 6-fluoro-N4-(2-fluoro-phenyl)-quinoline-3,4-diamine (Example 19e) in 8 ml triethylorthoformate are heated at 160° C. for 3 h. The cold solution is evaporated to dryness, and the residue is dissolved in hot ethyl acetate. By adding hexane to this solution, the title compound precipitates. The compound is filtered off and dried overnight at 60° C. (high vacuum). mp: 162-163° C.; MS: 282 (M*+1); HPLC: tret=7.26 min (Grad 1).

Workup

  1. customThe cold solution is evaporated to dryness
  2. dissolutionthe residue is dissolved in hot ethyl acetate
  3. additionBy adding hexane to this solution
  4. customthe title compound precipitates
  5. filtrationThe compound is filtered off
  6. customdried overnight at 60° C. (high vacuum)
  7. customtret=7.26 min (Grad 1)

Sources & evidence

ORD record
ord-b457fe2fa7504717a41c3f30f8411f4b
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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