3-Quinolinecarboxaldehyde → 5-Ethyl-2-fluoro-4-[3-(5-quinolin-3-ylmethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol

HRID 340028Notes

Reaction equation

HRID 340028 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.Br.Br.Br.[CH2:16]([C:18]1[C:19]([C:26]2[CH:34]=[C:33]3[C:29]([C:30]([C:35]4[NH:36][C:37]5[CH2:42][CH2:41][NH:40][CH2:39][C:38]=5[N:43]=4)=[N:31][NH:32]3)=[CH:28][CH:27]=2)=[CH:20][C:21]([F:25])=[C:22]([OH:24])[CH:23]=1)[CH3:17]>>[CH2:16]([C:18]1[C:19]([C:26]2[CH:34]=[C:33]3[C:29]([C:30]([C:35]4[NH:36][C:37]5[CH2:42][CH2:41][N:40]([CH2:11][C:3]6[CH:2]=[N:1][C:10]7[C:5]([CH:4]=6)=[CH:6][CH:7]=[CH:8][CH:9]=7)[CH2:39][C:38]=5[N:43]=4)=[N:31][NH:32]3)=[CH:28][CH:27]=2)=[CH:20][C:21]([F:25])=[C:22]([OH:24])[CH:23]=1)[CH3:17]

Participants

3

Reactant 2

HCID 836413-QuinolinecarboxaldehydeHCID 1784192405-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazol[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt

Product 1

HCID 1784369135-Ethyl-2-fluoro-4-[3-(5-quinolin-3-ylmethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenolYield 20.9%

Procedure

The title compound was prepared from quinoline-3-carbaldehyde (31 mg, 198 μmol) and 5-ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt (Preparation 25, 50 mg, 132 μmol) using the method of Example 22. The crude material was purified by HPLC Method B to afford 14.3 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method B

Sources & evidence

ORD record
ord-79b4280397844b2caf3ee105e843399c
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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