4-Aminotetrahydropyran → HCID 67502392, compound

HRID 921541Notes

Reaction equation

HRID 921541 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].[O:30]1[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]1.CC1C2C(=NC=CC=2C2C=NC3C(C=2)=CC=CC=3)N(C2C=CC=CC=2C(N)=O)C=1>>[O:30]1[CH2:35][CH2:34][CH:33]([NH:36][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]([CH3:29])=[CH:11]3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 4192234-AminotetrahydropyranHCID 67500186HCID 67500186, compoundHCID 131734926HCID 131734926, compound

Product 1

HCID 67502392HCID 67502392, compoundYield 4%

Procedure

According to Example 1(6), a crude product of 2-(tetrahydro-2H-pyran-4-ylamino)-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 tetrahydro-2H-pyran-4-amine instead of trans-aminocyclohexanol and was used in the subsequent reaction without being purified. According to Example 1(7), compound (53) (the second stage yield: 4%) was prepared as a white solid using 2-(tetrahydro-2H-pyran-4-ylamino)-4-{(3-methyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}benzonitrile instead of compound (1f). By this reaction, compound (54) (the second stage yield: 21%) was prepared as a white solid.

Workup

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

Sources & evidence

ORD record
ord-289c77353fb64c1f88fc483e79411dbe
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

Loading…