Methanol → 1-(2-Chloroethyl)-3-(4-cyclopropylpyridin-3-yl)urea

HRID 572370Notes

Reaction equation

HRID 572370 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH:7]1([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[NH2:16])[CH2:9][CH2:8]1.CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[CH:7]1[CH2:9][CH2:8]1)=[O:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 160352-Chloroethyl isocyanateHCID 668019694-Cyclopropylpyridin-3-amine

Product 1

HCID 867296631-(2-Chloroethyl)-3-(4-cyclopropylpyridin-3-yl)ureaYield 30%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

1-Chloro-2-isocyanatoethane (472 mg, 4.477 mmol) was added drop wise to a stirred mixture of 4-cyclopropylpyridin-3-amine (I-1b: 400 mg, 2.78 mmol) in toluene (10 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (10% methanol in CHCl3). The crude product was concentrated and purified by column chromatography on silica gel (2% methanol in CHCl3) afforded 200 mg of the product (28% yield).

Workup

  1. concentrationThe crude product was concentrated
  2. custompurified by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-a614df555db6404ba38c22d682c3b7d6
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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