Diisopropylethylamine → 4-[2-(5-Cyano-thiazol-2-ylamino)-5-methyl-pyridin-4-ylmethyl]-piperazine-1-carboxylic acid methylamide

HRID 1813999Notes

Reaction equation

HRID 1813999 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([NH:10][C:11]2[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=2)[CH:4]=1.[Cl-].[CH3:19][NH:20][C:21]([N:23]1[CH2:28][CH2:27][NH2+:26][CH2:25][CH2:24]1)=[O:22].C(N(C(C)C)CC)(C)C>CS(C)=O>[CH3:19][NH:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:2][C:3]2[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([NH:10][C:11]3[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=3)[CH:4]=2)[CH2:25][CH2:24]1)=[O:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 225043102-(4-Chloromethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrileHCID 695511324-Methylcarbamoyl-piperazin-1-ium chloride

Product 1

HCID 101772454-[2-(5-Cyano-thiazol-2-ylamino)-5-methyl-pyridin-4-ylmethyl]-piperazine-1-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(4-Chloromethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (9-9, 0.204 g, 0.771 mmol) and 4-methylcarbamoyl-piperazin-1-ium chloride (4-3, 0.277 g, 1.54 mmol) were dissolved in 2 mL DMSO. Diisopropylethyl amine (0.537 mL, 3.08 mmol) was added and the reaction was stirred for 3.5 hours. The reaction mixture was then directly loaded onto a reverse phase purification system to afford the titled compound, 9-10, as the TFA salt. 1H NMR (CD3OD) δ 8.35 (s, 1H), 8.02 (s, 1H), 7.16 (s, 1H), 4.25 (s, 2H), 3.37 (bs, 4H), 3.24 (bs, 4H), 2.73 (s, 3H), 2.39 (s, 3H). MS [M+H]+=372.1. 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-chloro-3-methyl-pyridine (10-1)

Workup

  1. customThe reaction mixture was then directly loaded onto a reverse phase purification system

Sources & evidence

ORD record
ord-07715ed2afce4333b48ccc4c4312589e
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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