Acetic acid--water (1/1) → 1-Cyclopropyl-3-(3-fluoro-4-(2-(6-formylpyridin-3-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

HRID 1400900Notes

Reaction equation

HRID 1400900 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[N:12]=[CH:11][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)=[CH:9][CH:8]=1.CC(O)=O.O>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:11]=[N:12][C:7]([CH:2]=[O:1])=[CH:8][CH:9]=5)[S:21][C:20]=34)=[C:24]([F:36])[CH:25]=2)=[O:31])[CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 674423941-(4-(2-(6-(1,3-Dioxan-2-yl)pyridin-3-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-cyclopropylurea

Product 1

HCID 866585971-Cyclopropyl-3-(3-fluoro-4-(2-(6-formylpyridin-3-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)ureaYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 281 (2.71 mg, 5.35 mmol) in a mixture AcOH/water (32 mL/8 mL) was heated at 90° C. for 29 h. After cooling to RT the reaction mixture was diluted with water to form a precipitate that was collected by filtration and dried under vacuum to afford the title compound 282 (2.25 g, 5.02 mmol, 94% yield) as a brown solid. MS (m/z): 449.2 (M+H).

Workup

  1. customto form a precipitate that
  2. filtrationwas collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a43b822d30cb4989af3e2bcb1cb7635a
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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