2-Amino-6-methylpyridine → 3-Isothiocyanato-2-methoxypyridine

HRID 2244394Notes

Reaction equation

HRID 2244394 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10]2[S:14]C=NC=2C(O)=O)=[CH:7][CH:6]=[CH:5][N:4]=1.CC1N=C(N)C=CC=1.COC1C(N)=CC=CN=1>>[N:9]([C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)=[C:10]=[S:14]

Participants

4

Reactant 3

HCID 157652-Amino-6-methylpyridineHCID 27374883-Amino-2-methoxypyridineHCID 68406549HCID 68406549, compound

Product 1

HCID 544880893-Isothiocyanato-2-methoxypyridine

Procedure

The title compound, MS (ISP): m/e=342.1 (M+H+), was prepared as for example 1, steps A to C. Step A was performed using 3-isothiocyanato-2-methoxy-pyridine and yielded 5-(2-methoxy-pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester. This was hydrolized in step B to 5-(2-methoxy-pyridin-3-ylamino)-thiazole-4-carboxylic acid, which was reacted with 6-methyl-pyridin-2-ylamine in step C. 3-Isothiocyanato-2-methoxy-pyridine was prepared as in example 96, starting from 2-methoxy-pyridin-3-ylamine.

Sources & evidence

ORD record
ord-0c02e9250b324788a5dbb8c0b07bdbec
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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