2-Amino-6-bromopyridine → [5-(4-Fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine

HRID 451379Notes

Reaction equation

HRID 451379 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[S:4][N:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]3[N:27]=[C:28]([NH2:30])[N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.NC1C=CC=C(Br)N=1>>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]3[N:27]=[C:28]([NH:30][CH:10]4[CH2:11][CH2:12][N:7]([C:5]5[S:4][N:3]=[C:2]([CH3:1])[N:6]=5)[CH2:8][CH2:9]4)[N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 3008092-Amino-6-bromopyridineHCID 445559165-(4-Fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamineHCID 592585101-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one

Product 1

HCID 53354634[5-(4-Fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine

Procedure

Prepared in analogy to example 1 step h) starting from 1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-one (example 1c) and 5-(4-fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine. The latter compound can be prepared in analogy to example 1 steps d-f) starting from 2-amino-6-bromo-pyridine. The title compound was obtained as a white solid.

Workup

  1. customPrepared in analogy to example 1 step h)
  2. customThe latter compound can be prepared in analogy to example 1 steps d-f)

Sources & evidence

ORD record
ord-9e4e645b22c44716966971d3772be088
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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