Acetoxyacetic acid → 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 1400921Notes

Reaction equation

C1(NC(=O)NC2C=CC(OC3C=CN=C4C=C(C5N=CN(CCN6CCN(C(OC(C)(C)C)=O)CC6)C=5)SC=34)=C(F)C=2)CC1.C1(NC(NC2C=CC(OC3C=CN=C4C=C(C5C=CC(CN6CCNCC6)=CN=5)SC=34)=C(F)C=2)=O)CC1.C(OCC(O)=O)(=O)C.C([O:93][CH2:94][C:95]([N:97]([CH2:102][C:103]1[CH:104]=[N:105][C:106]([C:109]2[S:117][C:116]3[C:111](=[N:112][CH:113]=[CH:114][C:115]=3[O:118][C:119]3[CH:120]=[N:121][C:122]([NH:125][C:126]([NH:128][CH:129]4[CH2:131][CH2:130]4)=[O:127])=[CH:123][CH:124]=3)[CH:110]=2)=[CH:107][CH:108]=1)[CH2:98][CH2:99][O:100][CH3:101])=[O:96])(=O)C>>[CH:129]1([NH:128][C:126](=[O:127])[NH:125][C:122]2[N:121]=[CH:120][C:119]([O:118][C:115]3[CH:114]=[CH:113][N:112]=[C:111]4[CH:110]=[C:109]([C:106]5[N:105]=[CH:104][C:103]([CH2:102][N:97]([CH2:98][CH2:99][O:100][CH3:101])[C:95](=[O:96])[CH2:94][OH:93])=[CH:108][CH:107]=5)[S:117][C:116]=34)=[CH:124][CH:123]=2)[CH2:130][CH2:131]1

Participants

Reactant 4

HCID 83766Acetoxyacetic acid

HCID 67440535tert-butyl 4-(2-(4-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate

HCID 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

HCID 674423881-Cyclopropyl-3-(3-fluoro-4-(2-(5-(piperazin-1-ylmethyl)pyridin-2-yl)thieno[3,2-b]-pyridin-7-yloxy)phenyl)urea2×

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 309 (example 167) and 310 (example 168) were prepared by reacting compounds 307 (scheme 68) and compound 49 (scheme 15) with acetoxyacetic acid, similarly to compound 30 (scheme 13). Compound 311 (example 169) was synthesized by following the procedures described above for the synthesis of compound 49 (scheme 15). Compounds 312 (example 170) and 313 (example 171) were obtained similarly to compound 31 (scheme 13). Compound 314 (example 172) was synthesized by following the procedures described above for the synthesis of compound 75 (scheme 20).

Workup

customCompounds 309 (example 167) and 310 (example 168) were prepared
customCompound 311 (example 169) was synthesized

Sources & evidence

ORD record: ord-d839a54d74cb4d2889266850b5236450
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906852B2

Reaction notes

Loading…