Cyclobutanone → HCID 11950505, compound

HRID 549249Notes

Reaction equation

C([C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[C:10](=[N:26][N:27]([CH2:30][CH3:31])[C:28]=3[CH3:29])[C:11]([N:19](C([O-])=O)C([O-])=O)=[N:12][C:13]=2[C:14]=1C(C)(C)C)(C)(C)C.C(C1C=CC2C3C(=NN(CCC)C=3C)C(N(C([O-])=O)C([O-])=O)=NC=2C=1C(C)(C)C)(C)(C)C.[O:64]=[C:65]1[CH2:70][CH2:69][S:68][CH2:67][CH2:66]1.C1(=O)CCC1>>[NH2:19][C:11]1[C:10]2=[N:26][N:27]([CH2:30][CH3:31])[C:28]([CH2:29][C:65]3([OH:64])[CH2:70][CH2:69][S:68][CH2:67][CH2:66]3)=[C:9]2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:14][C:13]=2[N:12]=1

Participants

Reactant 4

HCID 14496Cyclobutanone

HCID 66173Tetrahydrothiopyran-4-one

HCID 86631991HCID 86631991, compound

HCID 86631992HCID 86631992, compound

Product 1

HCID 11950505HCID 11950505, compound

Procedure

4-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]tetrahydro-2H-thiopyran-4-ol was prepared according to the method of Example 1 Part F using di(tert-butyl)2-ethyl-1-methyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate in lieu of di(tert-butyl)1-methyl-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate and 4-oxothiane in lieu of cyclobutanone. The crude product was recrystallized from acetonitrile to provide 0.475 g of 4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]tetrahydro-2H-thiopyran-4-ol as a white powder, mp 251.5-255° C.

Workup

custom4-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]tetrahydro-2H-thiopyran-4-ol was prepared
customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record: ord-3366505393c64a5783683c1d1cac8fc8
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943636B2

Reaction notes

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