4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamide → 4-(7-(2-Fluoro-4-(1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridazine-5-carboxamido)phenoxy)thieno[3,2-b]pyridin-2-yl)benzoic acid

HRID 1676368Notes

Reaction equation

HRID 1676368 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:25]=[CH:24][C:19]([C:20](NC)=[O:21])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:28])[CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[C:41](=[O:42])[C:40]([C:43](F)=[O:44])=[CH:39][CH:38]=[N:37]2)=[CH:32][CH:31]=1.FC1C=CC(NC(C2(C(F)=O)CC2)=[O:55])=CC=1>O>[F:28][C:4]1[CH:3]=[C:2]([NH:1][C:43]([C:40]2[C:41](=[O:42])[N:36]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)[N:37]=[CH:38][CH:39]=2)=[O:44])[CH:27]=[CH:26][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:55])=[O:21])=[CH:18][CH:17]=3)[S:15][C:8]=12

Participants

5

Reactant 3

HCID 673486984-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamideHCID 866146491-((4-Fluorophenyl)carbamoyl)cyclopropanecarbonyl fluorideHCID 866146532-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carbonyl fluoride

Product 1

HCID 673452974-(7-(2-Fluoro-4-(1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridazine-5-carboxamido)phenoxy)thieno[3,2-b]pyridin-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared according to the procedure for Example 112, Step B substituting 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)benzoic acid (1.25 g, 3.29 mmol) for 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamide and 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carbonyl fluoride (1.70 g, 5.75 mmol) for 1-((4-fluorophenyl)carbamoyl)cyclopropanecarbonyl fluoride. When the reaction was complete, water (20 mL) was added and the product (1.59 g, 80%) was collected by filtration to get a brown solid. LRMS (esi+) 597 m/z (M+1) detected.

Workup

  1. customPrepared
  2. filtrationthe product (1.59 g, 80%) was collected by filtration
  3. customto get a brown solid

Sources & evidence

ORD record
ord-ac1e1f7b52174f83a83d7153cffcfe2a
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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