1-(4-(2-(5-((Azetidin-3-yloxy)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-cyclopropylurea → N-((6-(7-(6-(3-cyclopropylureido)pyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-2-hydroxy-N-(2-methoxyethyl)acetamide

HRID 1400933Notes

Reaction equation

HRID 1400933 reaction equation
N1CC(OCC2C=CC(C3SC4C(=NC=CC=4OC4C=CC(NC(NC5CC5)=O)=CC=4F)C=3)=NC=2)C1.C([O:40][CH2:41][C:42]([N:44]([CH2:49][C:50]1[CH:51]=[N:52][C:53]([C:56]2[S:64][C:63]3[C:58](=[N:59][CH:60]=[CH:61][C:62]=3[O:65][C:66]3[CH:67]=[N:68][C:69]([NH:72][C:73]([NH:75][CH:76]4[CH2:78][CH2:77]4)=[O:74])=[CH:70][CH:71]=3)[CH:57]=2)=[CH:54][CH:55]=1)[CH2:45][CH2:46][O:47][CH3:48])=[O:43])(=O)C>>[CH:76]1([NH:75][C:73](=[O:74])[NH:72][C:69]2[N:68]=[CH:67][C:66]([O:65][C:62]3[CH:61]=[CH:60][N:59]=[C:58]4[CH:57]=[C:56]([C:53]5[N:52]=[CH:51][C:50]([CH2:49][N:44]([CH2:45][CH2:46][O:47][CH3:48])[C:42](=[O:43])[CH2:41][OH:40])=[CH:55][CH:54]=5)[S:64][C:63]=34)=[CH:71][CH:70]=2)[CH2:77][CH2:78]1

Participants

3

Reactant 2

HCID 674417991-(4-(2-(5-((Azetidin-3-yloxy)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-cyclopropylureaHCID 674421792-(((6-(7-(6-(3-Cyclopropylureido)pyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)(2-methoxyethyl)amino)-2-oxoethyl acetate

Product 1

HCID 67442923N-((6-(7-(6-(3-cyclopropylureido)pyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-2-hydroxy-N-(2-methoxyethyl)acetamide

Procedure

Compounds 411-412 (examples 260-261) were prepared in one step by reacting the amine precursor 401 (table 31), similarly to compound 30 (scheme 13). Compound 413 (example 262) was obtained similarly to compound 31 (scheme 13). Compounds 414-415 (examples 263-264) were prepared in two steps by reacting the corresponding amine precursors 402 (table 31) and 405 (scheme 76), similarly to compound 31 (scheme 13).

Workup

  1. customCompounds 411-412 (examples 260-261) were prepared in one step

Sources & evidence

ORD record
ord-a3216e3e763e44e0bf44fe58708ef8fa
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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