Cyclohexanone → HCID 57750722, compound

HRID 549248Notes

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.[C:64]1(=[O:70])[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]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:64]3([OH:70])[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]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 7967Cyclohexanone

HCID 14496Cyclobutanone

HCID 86631991HCID 86631991, compound

HCID 86631992HCID 86631992, compound

Product 1

HCID 57750722HCID 57750722, compound

Procedure

1-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]cyclohexanol 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-ylimidodicabonate and cyclohexanone in lieu of cyclobutanone. The crude product was recrystallized from acetonitrile to provide 0.560 g of 1-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]cyclohexanol as a white powder, mp 211.5-213° C.

Workup

custom1-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]cyclohexanol was prepared
customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record: ord-fffe5d46ba0d4b279078266d379073b0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943636B2

Reaction notes

Loading…