Tetrahydro-4H-pyran-4-one → 4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

HRID 549247Notes

Reaction equation

HRID 549247 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.[O:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1.C(C1C=CC2C3C(=NN(CCC)C=3C)C(N(C([O-])=O)C([O-])=O)=NC=2C=1C(C)(C)C)(C)(C)C>>[NH2:19][C:11]1[C:10]2=[N:26][N:27]([CH2:30][CH3:31])[C:28]([CH2:29][C:35]3([OH:38])[CH2:36][CH2:37][O:32][CH2:33][CH2:34]3)=[C:9]2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:14][C:13]=2[N:12]=1

Participants

4

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 86631991HCID 86631991, compound2×HCID 86631992HCID 86631992, compound

Product 1

HCID 119559964-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

Procedure

Di(tert-butyl)2-ethyl-1-methyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate was reacted with tetrahydro-4H-pyran-4-one according to the method of Example 2 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. The crude product was recrystallized acetonitrile provide 0.349 g 4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as off-white crystals, mp 253-255° C.

Workup

  1. customThe crude product was recrystallized acetonitrile

Sources & evidence

ORD record
ord-f084cca6e10d4db485219d99fb740fb5
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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