4-[3-Fluoro-5-(1-phenyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile → 4-[3-Fluoro-5-(1-methyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075653Notes

Reaction equation

HRID 2075653 reaction equation
CC1N2C3C(C=CC2=CN=1)=CC(SC1C=C(C2(O)CCOCC2)C=CC=1)=CC=3.COC1(C2C=C(SC3C=C4C(=CC=3)N3C(C)=NC=C3C=C4)C=CC=2)CCOCC1.[F:58][C:59]1[CH:60]=[C:61]([C:85]2([C:91]#[N:92])[CH2:90][CH2:89][O:88][CH2:87][CH2:86]2)[CH:62]=[C:63]([S:65][C:66]2[CH:67]=[C:68]3[C:73](=[CH:74][CH:75]=2)[N:72]2[C:76]([C:79]4C=CC=CC=4)=[N:77][CH:78]=[C:71]2[CH:70]=[CH:69]3)[CH:64]=1.FC1C=C(C2(C(N)=O)CCOCC2)C=C(SC2C=C3C(=CC=2)N2C(C4C=CC=CC=4)=NC=C2C=C3)C=1>>[F:58][C:59]1[CH:60]=[C:61]([C:85]2([C:91]#[N:92])[CH2:90][CH2:89][O:88][CH2:87][CH2:86]2)[CH:62]=[C:63]([S:65][C:66]2[CH:67]=[C:68]3[C:73](=[CH:74][CH:75]=2)[N:72]2[C:76]([CH3:79])=[N:77][CH:78]=[C:71]2[CH:70]=[CH:69]3)[CH:64]=1

Participants

5

Reactant 4

HCID 670906224-[3-Fluoro-5-(1-phenyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile2×HCID 670908267-[3-(4-Methoxy-tetrahydro-pyran-4-yl)-phenylsulfanyl]-1-methyl-imidazo[1,5-a]quinoline2×HCID 670909854-[3-Fluoro-5-(1-phenyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid amide2×HCID 670912874-[3-(1-Methyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-ol2×

Product 1

HCID 670908594-[3-Fluoro-5-(1-methyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Procedure

4-[3-(1-Methyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-ol (Compound 4-2); 7-[3-(4-Methoxy-tetrahydro-pyran-4-yl)-phenylsulfanyl]-1-methyl-imidazo[1,5-a]quinoline (Compound 4-3); 4-[3-Fluoro-5-(1-phenyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile (Compound 4-4); 4-[3-Fluoro-5-(1-phenyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid amide (Compound 4-5).

Sources & evidence

ORD record
ord-8be4b53da7e345218f32f2ccb28659ea
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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