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

HRID 340029

Reaction equation

HRID 340029 reaction equation
[O:1]([C:8]1[N:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.Br.Br.[CH2:19]([C:21]1[C:22]([C:29]2[CH:37]=[C:36]3[C:32]([C:33]([C:38]4[NH:39][C:40]5[CH2:45][CH2:44][NH:43][CH2:42][C:41]=5[N:46]=4)=[N:34][NH:35]3)=[CH:31][CH:30]=2)=[CH:23][C:24]([F:28])=[C:25]([OH:27])[CH:26]=1)[CH3:20]>>[CH2:19]([C:21]1[C:22]([C:29]2[CH:37]=[C:36]3[C:32]([C:33]([C:38]4[NH:39][C:40]5[CH2:45][CH2:44][N:43]([CH2:14][C:11]6[CH:12]=[N:13][C:8]([O:1][C:2]7[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=7)=[CH:9][CH:10]=6)[CH2:42][C:41]=5[N:46]=4)=[N:34][NH:35]3)=[CH:31][CH:30]=2)=[CH:23][C:24]([F:28])=[C:25]([OH:27])[CH:26]=1)[CH3:20]

Participants

3

Reactant 2

HCID 27765006-PhenoxynicotinaldehydeHCID 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 1784369105-Ethyl-2-fluoro-4-{3-[5-(6-phenoxy-pyridin-3-ylmethyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-6-yl}-phenolYield 33.4%

Procedure

The title compound was prepared from 6-phenoxy-pyridine-3-carbaldehyde (39 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 A to afford 24.7 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method A

Sources & evidence

ORD record
ord-acae3ef4fa7c48fe9a6ae733efdca4ba
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Linked notes

Loading…