1-(4-(2-(5-(1,3-Dioxan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-cyclopropylurea → 1-Cyclopropyl-3-(3-fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

HRID 1026809Notes

Reaction equation

HRID 1026809 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][CH:33]4[CH2:35][CH2:34]4)=[O:31])=[CH:25][C:24]=3[F:36])[CH:14]=2)=[N:11][CH:12]=1>CC(C)=O.O.C(O)(C(F)(F)F)=O>[CH:33]1([NH:32][C:30]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][C:19]3[CH:18]=[CH:17][N:16]=[C:15]4[CH:14]=[C:13]([C:10]5[CH:9]=[CH:8][C:7]([CH:2]=[O:1])=[CH:12][N:11]=5)[S:21][C:20]=34)=[C:24]([F:36])[CH:25]=2)=[O:31])[CH2:34][CH2:35]1

Participants

3

Reactant 1

HCID 442299041-(4-(2-(5-(1,3-Dioxan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-cyclopropylurea

Product 1

HCID 582365791-Cyclopropyl-3-(3-fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)ureaYield 85%

Reagents, catalysts & solvents 1

HCID 86652750acetone water TFASolvent

Procedure

A suspension of 320 (0.65 g, 1.3 mmol) in 5:2:1 acetone/water/TFA (100 mL) was heated to reflux for 6 h. The mixture was then cooled and concentrated. The resulting solid residue was suspended in water, isolated by suction filtration, washed with ethyl acetate and dried in vacuo yielding 321 (0.49 g, 1.1 mmol, 85% yield) which was used without further purification in the next step. MS: 449.0 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated
  5. customisolated by suction filtration
  6. washwashed with ethyl acetate
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b44dbcc2c2cc40d0a8ff39630455d3fe
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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