4-Amino-1-butanol → HCID 67500594, compound

HRID 921542Notes

Reaction equation

HRID 921542 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]([CH3:29])=[CH:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35]>>[OH:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:30][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]([CH3:29])=[CH:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 258684-Amino-1-butanolHCID 67500186HCID 67500186, compound

Product 1

HCID 67500594HCID 67500594, compoundYield 35%

Procedure

According to Example 1(6), a crude product of 2-(4-hydroxybutylamino)-4-{3-methyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}benzonitrile was prepared using compound (40f) instead of compound (1e) and using 4-amino-1-butanol instead of trans-aminocyclohexanol and was used in the subsequent reaction without being purified. According to Example 1(7), compound (55) (the second stage yield: 35%) was prepared as a white solid using 2-(4-hydroxybutylamino)-4-{(3-methyl-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. customwas prepared as a white solid

Sources & evidence

ORD record
ord-f4e2f656845e4280899cf99b4f571d31
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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