HCID 67500502, compound → HCID 178440309, compound

HRID 921530Notes

Reaction equation

HRID 921530 reaction equation
BrC1C=C(N2C3=NC=CC(C4[O:20]C=CC=4)=C3C(C(C)C)=N2)C=CC=1C#N.[OH:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([NH:34][C:35]2[CH:42]=[C:41]([N:43]3[C:47]4=[N:48][CH:49]=[CH:50][C:51]([C:52]5[O:53][CH:54]=[CH:55][CH:56]=5)=[C:46]4[C:45]([CH:57]([CH3:59])[CH3:58])=[N:44]3)[CH:40]=[CH:39][C:36]=2[C:37]#[N:38])[CH2:30][CH2:29]1>>[OH:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([NH:34][C:35]2[CH:42]=[C:41]([N:43]3[C:47]4=[N:48][CH:49]=[CH:50][C:51]([C:52]5[O:53][CH:54]=[CH:55][CH:56]=5)=[C:46]4[C:45]([CH:57]([CH3:59])[CH3:58])=[N:44]3)[CH:40]=[CH:39][C:36]=2[C:37]([NH2:38])=[O:20])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 67500502HCID 67500502, compoundHCID 178440307HCID 178440307, compound

Product 1

HCID 178440309HCID 178440309, compoundYield 59%

Procedure

According to Example 1(6), a crude product of 2-(trans-4-hydroxycyclohexylamino)-4-{(3-isopropyl-4-(furan-2-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile was prepared using compound (10a) instead of compound (1e) and was used in the subsequent reaction without being purified. According to Example 1(7), compound (10) (the second stage yield: 59%) was prepared as a white solid using 2-(trans-4-hydroxycyclohexylamino)-4-{3-isopropyl-4-(furan-2-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile instead of compound (1f).

Workup

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

Sources & evidence

ORD record
ord-b9e347bc3b614c23a85b6903bac2c456
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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