Cyclobutanone → HCID 67157619, compound

HRID 549250Notes

Reaction equation

HRID 549250 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([C:36]1[CH:37]=[CH:38][C:39]2[C:40]3[C:41](=[N:57][N:58]([CH2:61][CH2:62]C)[C:59]=3C)[C:42]([N:50](C([O-])=O)C([O-])=O)=[N:43][C:44]=2[C:45]=1C(C)(C)C)(C)(C)C.[O:64]=[C:65]1[CH2:70][CH2:69][N:68]([C:71](OC(C)(C)C)=O)[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][NH: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.[NH2:50][C:42]1[C:41]2=[N:57][N:58]([CH2:61][CH3:62])[C:59]([CH2:71][N:68]3[CH2:67][CH2:66][CH:65]([OH:64])[CH2:70][CH2:69]3)=[C:40]2[C:39]2[CH:38]=[CH:37][CH:36]=[CH:45][C:44]=2[N:43]=1

Participants

6

Reactant 4

HCID 14496CyclobutanoneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 86631991HCID 86631991, compoundHCID 86631992HCID 86631992, compound

Product 2

HCID 67157619HCID 67157619, compoundHCID 671577724-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol

Procedure

4-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-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 tert-butyl 4-oxopiperidine-1-carboxylate in lieu of cyclobutanone. The crude product was recrystallized from acetonitrile to provide 1.09 g of 1-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol as an off-white solid.

Workup

  1. customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-af28f4b922bf414bb6b53ef5135fc17d
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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