HCID 67502306, compound → HCID 178437007, compound

HRID 921548Notes

Reaction equation

HRID 921548 reaction equation
Br[C:2]1[CH:9]=[C:8]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([C:19]4[CH:20]=[N:21][C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[C:13]3[C:12]([CH2:29][CH3:30])=[CH:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C@H:31]1([NH2:38])[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33][CH2:32]1>>[NH2:37][C@H:34]1[CH2:35][CH2:36][C@H:31]([NH:38][C:2]2[CH:9]=[C:8]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][C:18]([C:19]5[CH:20]=[N:21][C:22]6[C:27]([CH:28]=5)=[CH:26][CH:25]=[CH:24][CH:23]=6)=[C:13]4[C:12]([CH2:29][CH3:30])=[CH:11]3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 67502306HCID 67502306, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178437007HCID 178437007, compoundYield 57%

Procedure

According to Example 1(6), a crude product of 2-(trans-4-aminocyclohexylamino)-4-{3-ethyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}benzonitrile was prepared using compound (41h) instead of compound (1e) and using trans-cyclohexane-1,4-diamine instead of trans-aminocyclohexanol and was used in the subsequent reaction without being purified. According to Example 1(7), a compound (the second stage yield: 57%) was prepared as a white solid using 2-(trans-4-aminocyclohexylamino)-4-{(3-ethyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}benzonitrile instead of compound (1f).

Workup

  1. customwas used in the subsequent reaction
  2. customwithout being purified
  3. customa compound (the second stage yield: 57%) was prepared as a white solid

Sources & evidence

ORD record
ord-542af570a5324f97a6d20daa07a5a72e
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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