HCID 54299500, compound → N-[4-(6-Chloro-3-pyridinyl)-2-pyrimidinyl]-1H-benzimidazol-2-amine

HRID 2289491Notes

Reaction equation

HRID 2289491 reaction equation
[NH:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[C:2]([NH2:4])=[NH:3].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH:22]=[CH:23]N(C)C)=[CH:17][N:16]=1>CC(O)C>[N:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[NH:6][C:5]=1[NH:1][C:2]1[N:4]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[N:16][CH:17]=2)[CH:22]=[CH:23][N:3]=1

Participants

4

Reactant 2

HCID 54299500HCID 54299500, compoundHCID 1785125941-(1H-benzimidazol-2-yl)guanidine

Product 1

HCID 18697940N-[4-(6-Chloro-3-pyridinyl)-2-pyrimidinyl]-1H-benzimidazol-2-amineYield 13.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-guanidinobenzimidazole (0.83 g, 4.75 mmol) and 1-(2-chloropyrid-5-yl)-3-dimethylamino-2-propen-1-one (1.00 g, 4.75 mmol) in propan-2-ol (10 ml) was refluxed for 18 h. The solid which formed on cooling to room temperature was collected and washed with cold propan-2-ol to afford the title compound (205 mg) as a white solid m.p. 308-311°. δH (d6DMSO) 7.06 (2H, m), 7.45 (2H, m), 7.69 (1H, d, J 5.3 Hz), 7.74 (1H, d, J 8.4 Hz), 8.59 (1H, dd, J 2.5, 8.4 Hz), 8.75 (1H, d, J 5.2 Hz), 9.21 (1H, d, J 1.9 Hz) and 11.30 (1H, br s).

Workup

  1. customThe solid which formed
  2. customwas collected
  3. washwashed with cold propan-2-ol

Sources & evidence

ORD record
ord-2949d6bd0b7e4d88a7c220060f8abc23
Source dataset
uspto-grants-2000_07
Patent number
US06093716

Reaction notes

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