2,2,5,5-Tetramethylmorpholine → 3-Fluoro-4-[3-methyl-4-(2,2,5,5-tetramethyl-morpholin-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol

HRID 2279116Notes

Reaction equation

HRID 2279116 reaction equation
FC1C=C(O)C=CC=1C1N=C2NN=C(C)C2=C(CN2CCNCC2C2C=CC=CC=2)C=1.C([O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[CH:47]=[C:48]([C:62](O)=O)[C:49]3[C:54]([CH3:55])=[N:53][N:52](C4CCCCO4)[C:50]=3[N:51]=2)=[C:42]([F:65])[CH:41]=1)C1C=CC=CC=1.[CH3:66][C:67]1([CH3:75])[O:72][CH2:71][C:70]([CH3:74])([CH3:73])[NH:69][CH2:68]1>>[F:65][C:42]1[CH:41]=[C:40]([OH:39])[CH:45]=[CH:44][C:43]=1[C:46]1[N:51]=[C:50]2[NH:52][N:53]=[C:54]([CH3:55])[C:49]2=[C:48]([CH2:62][N:69]2[C:70]([CH3:74])([CH3:73])[CH2:71][O:72][C:67]([CH3:75])([CH3:66])[CH2:68]2)[CH:47]=1

Participants

4

Reactant 3

HCID 288062332,2,5,5-TetramethylmorpholineHCID 866803216-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 1784344133-Fluoro-4-[3-methyl-4-(2-phenyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol

Product 1

HCID 1784344113-Fluoro-4-[3-methyl-4-(2,2,5,5-tetramethyl-morpholin-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol

Procedure

The title compound was prepared in analogy to Example 1 steps (d) to (g) starting from 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid and 2,2,5,5-tetramethyl-morpholine, however, in the last step only the THP-protecting group on the pyrazole ring was removed.

Workup

  1. customhowever, in the last step only the THP-protecting group on the pyrazole ring was removed

Sources & evidence

ORD record
ord-109e2ae26fbe4ef08f45c70eb95340f0
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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