3-Aminopyridine → HCID 11560023, compound

HRID 2244412Notes

Reaction equation

HRID 2244412 reaction equation
Br[C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([NH:10][C:11]1[N:16]=[C:15]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH:14]=[CH:13][CH:12]=1)=[O:9].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1>>[CH3:7][C:5]1[S:6][C:2]([NH:28][C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)=[C:3]([C:8]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH:14]=[CH:13][CH:12]=2)=[O:9])[N:4]=1

Participants

3

Reactant 2

HCID 100093-AminopyridineHCID 68406610HCID 68406610, compound

Product 1

HCID 11560023HCID 11560023, compound

Procedure

A solution of 5-bromo-2-methyl-thiazole-4-carboxylic (prepared as described in example 119, steps A to B) (0.13 g, 0.60 mmol) in dichloromethane (5.00 ml) and DMF (0.10 ml) was treated with thionyl chloride (0.08 g, 0.66 mmol) and stirred at room temperature for 4.5 h. After this time, 6-amino-pyridin-2-ylmethyl ester (0.10 g, 0.60 mmol) and DIPEA (0.16 g, 1.20 mmol) were added, and the mixture stirred for 30 min. The solvents were then evaporated and the residue purified by flash chromatography (heptane/ethyl acetate) to yield acetic acid 6-[(5-bromo-2-methyl-thiazole-4-carbonyl)-amino]-pyridin-2-ylmethyl ester (0.17 g, 76%) as a white solid, MS (ISP): m/e=372.0, 370.0 (M+H+). Acetic acid 6-[(5-bromo-2-methyl-thiazole-4-carbonyl)-amino]-pyridin-2-ylmethyl ester was then coupled with pyridin-3-ylamine in step B to yield the title compound.

Sources & evidence

ORD record
ord-0f55d3a42cea4220b97b0b65cae9d2a6
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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