Carbon Disulfide → 3-(2-ethoxyethyl)-2-[[4-(2-isothiocyanatoethyl)-1-piperazinyl]methyl]-3H-imidazo[4,5-b]pyridine

HRID 1708926Notes

Reaction equation

HRID 1708926 reaction equation
[C:1](=[S:3])=S.[CH2:4]([O:6][CH2:7][CH2:8][N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH2:27])[CH2:21][CH2:20]1)[CH3:5]>O1CCCC1>[CH2:4]([O:6][CH2:7][CH2:8][N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[CH2:18][N:19]1[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][N:27]=[C:1]=[S:3])[CH2:23][CH2:24]1)[CH3:5]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 199115154-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamine

Product 1

HCID 199114903-(2-ethoxyethyl)-2-[[4-(2-isothiocyanatoethyl)-1-piperazinyl]methyl]-3H-imidazo[4,5-b]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (-10° C.) mixture of 18 parts of carbon disulfide, 7.22 parts of N,N'-methanetetraylbis[cyclohexanamine] and 135 parts of tetrahydrofuran was added dropwise a solution of 12.9 parts of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamine in tetrahydrofuran. Upon complete addition, the temperature was allowed to reach room temperature. After stirring for 1 hour at room temperature, the mixture was evaporated, yielding 13.1 parts (100%) of 3-(2-ethoxyethyl)-2-[[4(2-isothiocyanatoethyl)-1-piperazinyl]methyl]-3H-imidazo[4,5-b]pyridine as a residue (compound 121)

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. customto reach room temperature
  4. stirringAfter stirring for 1 hour at room temperature
  5. customthe mixture was evaporated

Sources & evidence

ORD record
ord-6949548c972f4a98aecb6bdd6671b2c6
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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