N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide → 2,6-Difluoro-n-(3-{3-[2-({3-[1-(methylsulfonyl)ethyl]-phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamide

HRID 1159924Notes

Reaction equation

HRID 1159924 reaction equation
C1C2C(=CC=C(NC3N=C(C4C(C5C=C(NC(=O)C6C=CC=CC=6)C=CC=5)=NN5C=CC=CC=45)C=CN=3)C=2)CCN1.Cl[C:43]1[N:48]=[C:47]([C:49]2[C:50]([C:58]3[CH:59]=[C:60]([NH:64][C:65](=[O:74])[C:66]4[C:71]([F:72])=[CH:70][CH:69]=[CH:68][C:67]=4[F:73])[CH:61]=[CH:62][CH:63]=3)=[N:51][N:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=23)[CH:46]=[CH:45][N:44]=1.[CH3:75][S:76]([CH:79]([C:81]1[CH:82]=[C:83]([NH2:87])[CH:84]=[CH:85][CH:86]=1)[CH3:80])(=[O:78])=[O:77]>>[F:73][C:67]1[CH:68]=[CH:69][CH:70]=[C:71]([F:72])[C:66]=1[C:65]([NH:64][C:60]1[CH:61]=[CH:62][CH:63]=[C:58]([C:50]2[C:49]([C:47]3[CH:46]=[CH:45][N:44]=[C:43]([NH:87][C:83]4[CH:84]=[CH:85][CH:86]=[C:81]([CH:79]([S:76]([CH3:75])(=[O:78])=[O:77])[CH3:80])[CH:82]=4)[N:48]=3)=[C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][N:52]3[N:51]=2)[CH:59]=1)=[O:74]

Participants

4

Reactant 3

HCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamideHCID 59513880N-(3-{3-[2-(1,2,3,4-tetrahydro-7-isoquinolinylamino)-4-pyrimidinyl]-pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamideHCID 68644221HCID 68644221, compound

Product 1

HCID 445291022,6-Difluoro-n-(3-{3-[2-({3-[1-(methylsulfonyl)ethyl]-phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamide

Procedure

The title compound is racemic and may be prepared by a procedure similar to Example 27, Step D using N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide and racemic {3-[1-(methylsulfonyl)ethyl]-phenyl}amine. 1H NMR (400 MHz, DMSO-d6): δ 10.92 (s, 1H); 9.63 (s, 1H); 8.82 (d, 1H); 8.50 (d, 1H); 8.24 (d, 1H); 7.98 (s, 1H); 7.82 (d, 1H); 7.76 (br s, 2H); 7.56 (qt, 1H); 7.47 (t, 2H); 7.35 (d, 1H); 7.23 (m, 3H); 7.11 (t, 1H); 7.01 (d, 1H); 6.53 (d, 1H); 4.40 (m, 1H); 2.80 (s, 3H); 1.60 (d, 3H). HRMS (ESI): (M+H)+ calculated 625.1833, found 625.1828.

Workup

  1. custommay be prepared by a procedure similar to Example 27, Step D

Sources & evidence

ORD record
ord-cd15a1e8f1ce4aefb90916f4fab91dec
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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