4-Amino-1-butanol → HCID 131734928, compound

HRID 921549Notes

Reaction equation

HRID 921549 reaction equation
BrC1C=C(N2[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]3C(CC)=C2)C=CC=1C#N.[NH2:31][CH2:32][CH2:33][CH2:34][CH2:35]O.C(C1C2C(=NC=CC=2C2C=NC3C(C=2)=CC=CC=3)N([C:58]2[CH:65]=[CH:64][C:61]([C:62]#[N:63])=[C:60]([NH:66][CH2:67][CH2:68][CH2:69][CH2:70][OH:71])[CH:59]=2)C=1)C>>[CH2:34]([C:33]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][C:18]=2[C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:31]([C:59]2[C:60]([NH:66][CH2:67][CH2:68][CH2:69][CH2:70][OH:71])=[C:61]([CH:64]=[CH:65][CH:58]=2)[C:62]#[N:63])[CH:32]=1)[CH3:35]

Participants

4

Reactant 3

HCID 258684-Amino-1-butanolHCID 67500315HCID 67500315, compoundHCID 67502306HCID 67502306, compound

Product 1

HCID 131734928HCID 131734928, compoundYield 38%

Procedure

According to Example 1(6), a crude product of 4-{(3-ethyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}-2-(4-hydroxybutylamino)benzonitrile was prepared using compound (41h) 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 (74) (the second stage yield: 38%) was prepared as a white solid using 4-{3-ethyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}-2-(4-hydroxybutylamino)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-fa57e94193244a768fbfba83c5a563b2
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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