HCID 22031343, compound → HCID 22032328, compound

HRID 1792586Notes

Reaction equation

Br[C:2]1C=CC2N(C(C3SC(SC)=CC=3)=CN=2)C=1.CC1(C)C(C)(C)OB(C2C(C3C=CC(C(OC)=O)=CC=3)=NN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C=2)O1.[CH3:61][S:62][C:63]1[S:67][C:66]([C:68]2[N:72]3[CH:73]=[C:74]([C:77]4[C:78]([C:101]5[CH:110]=[CH:109][C:104]([C:105]([O:107][CH3:108])=[O:106])=[CH:103][CH:102]=5)=[N:79][N:80]([C:82]([C:95]5[CH:100]=[CH:99][CH:98]=[CH:97][CH:96]=5)([C:89]5[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=5)[C:83]5[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=5)[CH:81]=4)[CH:75]=[CH:76][C:71]3=[N:70][CH:69]=2)=[CH:65][CH:64]=1>>[CH3:61][S:62][C:63]1[S:67][C:66]([C:68]2[N:72]3[CH:73]=[C:74]([C:77]4[C:78]([C:101]5[CH:102]=[CH:103][C:104]([C:105]([O:107][CH2:108][CH3:2])=[O:106])=[CH:109][CH:110]=5)=[N:79][N:80]([C:82]([C:83]5[CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=5)([C:95]5[CH:100]=[CH:99][CH:98]=[CH:97][CH:96]=5)[C:89]5[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=5)[CH:81]=4)[CH:75]=[CH:76][C:71]3=[N:70][CH:69]=2)=[CH:65][CH:64]=1

Participants

Reactant 3

HCID 22031343HCID 22031343, compound2×

HCID 22031633HCID 22031633, compound

HCID 22032168HCID 22032168, compound

Product 1

HCID 22032328HCID 22032328, compound

Procedure

260 mg 6-bromo-3-[5-(methylsulfanyl)-2-thienyl]imidazo[1,2-a]pyridine (compound in Production Example 58) and 1 g mixture of methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate and methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate were reacted in the same manner as in Example 10, whereby 515 mg mixture of methyl 4-{4-[3-(5-methylsulfanylthiophen-2-yl)imidazo[1,2-a]-pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}benzoate and ethyl 4-{4-[3-(5-methylsulfanylthiophen-2-yl)imidazo[1,2-a]-pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}benzoate was obtained as a pale yellow amorphous. A mixture of 300 mg of this ester derivative, 1.3 mL of 1 N aqueous sodium hydroxide and 7 mL ethanol was stirred at 50° C. for 5 hours. An aqueous saturated ammonium chloride solution, ethylacetate, tetrahydrofuran and water were added to the reaction solution, and the organic layer was separated. To dissolve insolubles, dichloromethane and methanol were added to this organic layer which was then dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was subjected to azeotropic distillation with toluene to give 416 mg crude product of 4-{4-[3-(5-methylsulfanylthiophen-2-yl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}-benzoic acid as white crystals. From 414 mg of this carboxylic acid, 62 mg of the title compound was obtained as a pale yellow amorphous by the same reaction as in Example 361.

Sources & evidence

ORD record: ord-8283f3caa79d40a494434f9ecf3a4b04
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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