2-Morpholinoethylamine → 4-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(2-morpholinoethylamino)benzamide

HRID 921533Notes

Reaction equation

HRID 921533 reaction equation
C(C1C2C(=NC=CC=2C2C=NC3C(C=2)=CC=CC=3)N(C2C(NCCN3CC[O:37]CC3)=C(C=CC=2)C#N)N=1)(C)C.O1CCN(CCN)CC1.[CH:49]([C:52]1[C:60]2[C:55](=[N:56][CH:57]=[CH:58][C:59]=2[C:61]2[CH:62]=[N:63][C:64]3[C:69]([CH:70]=2)=[CH:68][CH:67]=[CH:66][CH:65]=3)[N:54]([C:71]2[CH:78]=[CH:77][C:74]([C:75]#[N:76])=[C:73]([NH:79][CH2:80][CH2:81][N:82]3[CH2:87][CH2:86][O:85][CH2:84][CH2:83]3)[CH:72]=2)[N:53]=1)([CH3:51])[CH3:50]>>[CH:49]([C:52]1[C:60]2[C:55](=[N:56][CH:57]=[CH:58][C:59]=2[C:61]2[CH:62]=[N:63][C:64]3[C:69]([CH:70]=2)=[CH:68][CH:67]=[CH:66][CH:65]=3)[N:54]([C:71]2[CH:78]=[CH:77][C:74]([C:75]([NH2:76])=[O:37])=[C:73]([NH:79][CH2:80][CH2:81][N:82]3[CH2:83][CH2:84][O:85][CH2:86][CH2:87]3)[CH:72]=2)[N:53]=1)([CH3:51])[CH3:50]

Participants

4

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 675001874-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(2-morpholinoethylamino)benzonitrileHCID 131734924(3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(2-morpholinoethylamino)benzonitrile

Product 1

HCID 498720814-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(2-morpholinoethylamino)benzamideYield 43%

Procedure

According to Example 1(6), 4-{(3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(2-morpholinoethylamino)benzonitrile was prepared using compound (6d) instead of compound (1e) and using 2-morpholinoethylamine instead of trans-aminocyclohexanol and was used in the subsequent reaction without being purified. According to Example 1(7), compound (31) (the second stage yield: 43%) was prepared as a white solid using 4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(2-morpholinoethylamino)benzonitrile instead of compound (1f).

Workup

  1. customwas prepared
  2. customwas used in the subsequent reaction
  3. customwithout being purified
  4. customwas prepared as a white solid

Sources & evidence

ORD record
ord-87792afcb37b403bbe3aaf22a8363dea
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

Loading…