3,4-Diaminopyridine → HCID 15037496, compound

HRID 1460542Notes

Reaction equation

HRID 1460542 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[C:3]([NH2:8])[CH:2]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[NH:26][CH:27]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][N:34]=[C:35]=[S:36])[CH2:28]2)=[CH:12][CH:11]=1>O1CCCC1>[NH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][C:3]=1[NH:8][C:35]([NH:34][CH2:33][CH2:32][N:29]1[CH2:30][CH2:31][CH:27]([NH:26][C:18]2[N:17]([CH2:16][C:13]3[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=2)[CH2:28]1)=[S:36]

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 15037493HCID 15037493, compound

Product 1

HCID 15037496HCID 15037496, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.8 parts of 3,4-pyridinediamine, 10.7 parts of 1-[(4-fluorophenyl)methyl]-N-[1-(2-isothiocyanatoethyl)-3-pyrrolidinyl]-1H-benzimidazol-2-amine and 90 parts of tetrahydrofuran was stirred and refluxed for 7 hours. The precipitated product was filtered off while hot, washed with a small amount of tetrahydrofuran and dried, yielding 6.5 parts (51%) of N-(4-amino-3-pyridinyl)-N'-[2-[3-[[1-[(4-fluorophenyl) methyl]-1H-benzimidazol-2-yl]amino]-1-pyrrolidinyl]ethyl]thiourea; mp. 225° C. (compound 177).

Workup

  1. temperaturerefluxed for 7 hours
  2. filtrationThe precipitated product was filtered off while hot,
  3. washwashed with a small amount of tetrahydrofuran
  4. customdried

Sources & evidence

ORD record
ord-38ed785dee114250844c3e2a7d1a70e3
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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