Sodium Hydroxide → HCID 178423413, compound

HRID 322019Notes

Reaction equation

HRID 322019 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([C:9]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[N:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH:30]=[CH:29][C:21]2[N:22]=[C:23]([NH:25][C:26]([NH2:28])=[NH:27])[NH:24][C:20]=2[CH:19]=1.[OH-].[Na+]>CO.O>[CH3:17][C:18]1[CH:30]=[CH:29][C:21]2[N:22]=[C:23]([N:25]=[C:26]3[NH:28][C:7]4([C:5]5[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=5)[NH:28][C:26](=[N:25][C:23]5[NH:24][C:20]6[CH:19]=[C:18]([CH3:17])[CH:30]=[CH:29][C:21]=6[N:22]=5)[NH:27][C:9]4([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][N:16]=4)[NH:27]3)[NH:24][C:20]=2[CH:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 68115Di-2-pyridylethanedioneHCID 178423417HCID 178423417, compound

Product 1

HCID 178423413HCID 178423413, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2,2′-pyridil (603 mg, 2.84 mmol) and 5-methyl-2-guanidinobenzimidazole (489 mg, 2.58 mmol) in methanol (17 mL) was treated with a solution of sodium hydroxide (113.6 mg, 2.84 mmol) in 2.8 mL of water. The title compound was isolated as a grey powder (450 mg, 63% yield). mp: 290-291° C. (dec); HPLC retention time 7.1 min (reversed phase, Beckman ultrasphere ODS 4.6 mm×25 cm column, 20 min gradient elution with 20:80 to 60:40 acetonitrile:water containing 0.1% TFA@2 mL/min); 1H NMR (300 MHz, d6-DMSO) δ11.3 (br s, NH, 2 H), 10.0 (br s, NH, 2 H), 8.5 (br s, NH, 2 H), 8.32 (d, J=4.2 Hz, 2 H), 7.54 (t, J=7.6 Hz, 2 H), 7.31 (d, J=7.6 Hz, 2 H), 7.16 (d, J=7.8 Hz, 2 H), 7.16-7.09 (m, 2 H), 7.09 (s, 2 H), 7.14 (br s, 2 H), 6.86 (d, J=7.8, Hz, 2 H), 2.34 (s, 6 H); MS (ESI) m/z 555 [M+H]+.

Sources & evidence

ORD record
ord-66ce686cb56f4eaca02d76a340be10cf
Source dataset
uspto-grants-2001_04
Patent number
US06211200B1

Reaction notes

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