3,4-Diaminopyridine → N-(4-amino-3-pyridinyl)-N'-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiourea

HRID 477664Notes

Reaction equation

HRID 477664 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[C:3]([NH2:8])[CH:2]=1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][N:33]=[C:34]=[S:35])[CH2:27][CH2:26]1>O1CCCC1>[NH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][C:3]=1[NH:8][C:34]([NH:33][CH2:32][CH2:31][N:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:16]2[N:15]([CH2:14][C:10]3[O:9][CH:13]=[CH:12][CH:11]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=2)[CH2:26][CH2:27]1)=[S:35]

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 148353051-(2-furanylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine

Product 1

HCID 14835314N-(4-amino-3-pyridinyl)-N'-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thioureaYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.4 parts of 3,4-pyridinediamine, 16 parts of 1-(2-furanylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine and 135 parts of tetrahydrofuran was stirred and refluxed overnight. The reaction mixture was evaporated in vacuo. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 18 parts (87%) of N-(4-amino-3-pyridinyl)-N'-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiourea (intermediate 133).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated in vacuo
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-d01359c29cf24eb2b7702bc019610066
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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