2-Amino-6-methylpyridine → HCID 11632079, compound

HRID 2244429Notes

Reaction equation

HRID 2244429 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[S:6][C:7]([NH:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[C:8]([C:10]([OH:12])=O)[N:9]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:51][C:52]1[N:57]=[C:56]([NH2:58])[CH:55]=[CH:54][CH:53]=1>CN(C)C=O>[CH3:51][C:52]1[N:57]=[C:56]([NH:58][C:10]([C:8]2[N:9]=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[S:6][C:7]=2[NH:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:12])[CH:55]=[CH:54][CH:53]=1

Participants

6

Reactant 4

HCID 157652-Amino-6-methylpyridineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68405890HCID 68405890, compound

Product 1

HCID 11632079HCID 11632079, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2-methoxy-ethyl)-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (0.032 g, 0.11 mmol) in dimethylformamide (1.00 ml) was treated with DIPEA (0.042 g, 0.33 mmol), TBTU (0.053 g, 0.16 mmol) and 6-methyl-pyridin-2-yl-amine (0.018 g, 0.16 mmol). The mixture was stirred at room temperature overnight, then purified by direct injection in preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid). The tide compound (0.011 g, 27%) was obtained as a white solid, MS (ISP): m/e=370.1 (M+H+).

Workup

  1. custompurified by direct injection in preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid)

Sources & evidence

ORD record
ord-e91b049ddfef40fe8b2724556cc50746
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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