Sodium Iodide → HCID 67012248, compound

HRID 2111788Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[O:22])=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:8][CH:7]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[OH:37].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C=O)C>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][NH:23][C:21]([C:19]2[CH:18]=[CH:17][C:16]3[N:12]([C:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:37][C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=5)=[CH:7][CH:8]=4)[CH:13]=[N:14][C:15]=3[CH:20]=2)=[O:22])[CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-[4-(3-Chloropropoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (185 mg, 0.44 mmol), 2-pyridinol (42 mg, 0.44 mmol), cesium carbonate (156 mg, 0.48 mmol) and sodium iodide (72 mg, 0.48 mmol) were dissolved in DMF (4 mL) and the mixture heated at 80° C. under N2 for 16 h. After this time the reaction mixture was concentrated in vacuo and subjected to reverse-phase preparative HPLC purification to afford isolation of N-pyridin-3-ylmethyl-1-{4-[3-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide; MS (ES+): m/z 480 [MH+] and 1-{4-[3-(2-Oxopyridin-1(2H)-yl)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide; MS (ES+): m/z 480 [MH+]

Workup

concentrationAfter this time the reaction mixture was concentrated in vacuo
customsubjected to reverse-phase preparative HPLC purification

Sources & evidence

ORD record: ord-1f78ecaa7b0a4709afd2a6569ba965c8
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521448B2

Reaction notes

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