4-Methylpiperazine-1-ethylamine → 1-(6-Thiocyanato-1,3-benzothiazol-2-yl)-3-[2-(4-methylpiperazin-1-yl)ethyl]urea

HRID 1035760Notes

Reaction equation

HRID 1035760 reaction equation
C1(O[C:8](=[O:22])[NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([S:19][C:20]#[N:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)C=CC=CC=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][NH2:32])[CH2:26][CH2:25]1>>[S:19]([C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([NH:9][C:8]([NH:32][CH2:31][CH2:30][N:27]3[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]3)=[O:22])[S:11][C:12]=2[CH:18]=1)[C:20]#[N:21]

Participants

3

Reactant 2

HCID 702844-Methylpiperazine-1-ethylamineHCID 53472570Phenyl(6-thiocyanato-1,3-benzothiazol-2-yl)carbamate

Product 1

HCID 866478811-(6-Thiocyanato-1,3-benzothiazol-2-yl)-3-[2-(4-methylpiperazin-1-yl)ethyl]urea

Procedure

The 1-(6-thiocyanato-1,3-benzothiazol-2-yl)-3-[2-(4-methylpiperazin-1-yl)ethyl]urea was prepared according to the method described in Example 9c, but using 982 mg of phenyl(6-thiocyanato-1,3-benzothiazol-2-yl)carbamate and 473 mg of 2-(4-methylpiperazin-1-yl)ethylamine. The residue obtained is chromatographed on a Merck cartridge (25 g of silica 15-40 μm), elution being carried out with a 90/10 mixture of dichloromethane/methanol. 1.13 g of 1-(6-thiocyanato-1,3-benzothiazol-2-yl)-3-[2-(4-methylpiperazin-1-yl)ethyl]urea are thus recovered in the form of a white solid, the characteristics of which are as follows:

Workup

  1. customThe residue obtained
  2. customis chromatographed on a Merck cartridge (25 g of silica 15-40 μm), elution
  3. additionbeing carried out with a 90/10 mixture of dichloromethane/methanol
  4. custom1.13 g of 1-(6-thiocyanato-1,3-benzothiazol-2-yl)-3-[2-(4-methylpiperazin-1-yl)ethyl]urea are thus recovered in the form of a white solid

Sources & evidence

ORD record
ord-d82a93871b5a478a981409592368c399
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Reaction notes

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