Diisopropylethylamine → 4-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-6-ethylpyridin-4-yl}methyl)-N-methylpiperazine-1-carboxamide

HRID 1814014Notes

Reaction equation

HRID 1814014 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)[CH:4]=1.[Cl-].[CH3:20][NH:21][C:22]([N:24]1[CH2:29][CH2:28][NH2+:27][CH2:26][CH2:25]1)=[O:23].C(N(C(C)C)C(C)C)C>CS(C)=O.O>[C:17]([C:14]1[S:13][C:12]([NH:11][C:5]2[CH:4]=[C:3]([CH2:2][N:27]3[CH2:28][CH2:29][N:24]([C:22]([NH:21][CH3:20])=[O:23])[CH2:25][CH2:26]3)[CH:8]=[C:7]([CH2:9][CH3:10])[N:6]=2)=[N:16][CH:15]=1)#[N:18]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 225042962-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrileHCID 695511324-Methylcarbamoyl-piperazin-1-ium chloride

Product 1

HCID 102001074-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-6-ethylpyridin-4-yl}methyl)-N-methylpiperazine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (0.113 g, 0.41 mmol) was dissolved in 2 mL DMSO. 1-[(Methylamino)carbonyl]piperazin-4-ium chloride (0.146 g, 0.81 mmol) and N-ethyl-N,N-diisopropylamine (0.283 mL, 1.63 mmol) were added and the solution was stirred for 24 hours. The reaction was diluted with water and the resulting precipitate was filtered and washed with water. The precipitate was purified by flash column chromatography (gradient, 5-10% MeOH/CH2Cl2). The fractions containing the desired compound were concentrated to dryness to afford the desired product 12-4.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customThe precipitate was purified by flash column chromatography (gradient, 5-10% MeOH/CH2Cl2)
  4. additionThe fractions containing the desired compound
  5. concentrationwere concentrated to dryness

Sources & evidence

ORD record
ord-c1c083e1210848f6b8da0a5ef0dcd9f7
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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