Toluene → N-(3-Fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamide

HRID 1047433Notes

Reaction equation

HRID 1047433 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:29]([C:31]4([C:34]([NH2:36])=[O:35])[CH2:33][CH2:32]4)=[O:30])=[CH:24][C:23]=3[F:43])[CH:13]=2)=[N:10][CH:11]=1.C1(C)C=CC=CC=1>CC(C)=O.O.C(O)(C(F)(F)F)=O>[F:43][C:23]1[CH:24]=[C:25]([N:28]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:29]([C:31]2([C:34]([NH2:36])=[O:35])[CH2:33][CH2:32]2)=[O:30])[CH:26]=[CH:27][C:22]=1[O:21][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][N:10]=3)[S:20][C:19]=12

Participants

6

Reactant 2

HCID 1140TolueneHCID 66599014N-(4-(2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Product 1

HCID 86635186N-(3-Fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamideYield 103%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Intermediate 41 (0.22 g, 0.37 mmol) was dissolved in acetone (50 mL) to give a colorless solution. The reaction mixture was diluted with water (20 mL) and TFA (2 mL), heated to reflux for 2 h, then cooled and concentrated. The precipitated product was isolated by suction filtration. A small amount of toluene (5 mL) was added to the wet solid, the mixture was concentrated to remove water azeotropically, and dried in vacuum to afford intermediate 42 (0.21 g, 103% yield, presumably as tri-fluoroacetate salt). MS (m/z): 553.2 (M+H).

Workup

  1. customto give a colorless solution
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. temperaturecooled
  5. concentrationconcentrated
  6. customThe precipitated product was isolated by suction filtration
  7. concentrationthe mixture was concentrated
  8. customto remove water azeotropically
  9. customdried in vacuum

Sources & evidence

ORD record
ord-94a04e6eef4f429e8e4050c5e3dc468b
Source dataset
uspto-grants-2013_10
Patent number
US08569503B2

Reaction notes

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