Formaldehyde → HCID 178423582, compound

HRID 415115Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:35])=[C:6]([NH:8][C:9]([C:11]2[N:12]=[CH:13][NH:14][C:15]=2[C:16]([NH:18][C:19]2[NH:23][C:22]3[C:24]([O:28][CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)=[O:17])=[O:10])[CH:7]=1.[C:36](#N)C.C=O.C([BH3-])#N.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:35])=[C:6]([NH:8][C:9]([C:11]2[N:12]=[CH:13][NH:14][C:15]=2[C:16]([NH:18][C:19]2[NH:23][C:22]3[C:24]([O:28][CH:29]4[CH2:34][CH2:33][N:32]([CH3:36])[CH2:31][CH2:30]4)=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)=[O:17])=[O:10])[CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

N4-(5-Bromo-2-methylphenyl)-N5-(7-(piperidin-4-yloxy)-1H-benzo[d]imidazol-2-yl)-1H-imidazole-4,5-dicarboxamide (0.1 mmol) was weighted out into a round bottomed flask and acetonitrile (5 mL) was added and the resulting solution was stirred at 25° C. Formaldehyde (1.0 mmol) and sodium cyanoborohydride (0.32 mmol) was added. The reaction mixture was kept neutral by the addition of acetic acid. After 2 hours, the reaction mixture was concentrated under reduced pressure. The crude product was purified via reverse phase HPLC (aqueous ammonium acetate/acetonitrile) to give N4-(5-bromo-2-methylphenyl)-N5-{7-[(1-methylpiperidin-4-yl)oxy]-1H-benzimidazol-2-yl}-1H-imidazole-4,5-dicarboxamide as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ 8.06 (s, 1H), 7.97 (s, 1H), 7.35 (m, 1H), 7.28 (d, 1H), 7.12 (dd, 1H), 6.99 (m, 1H), 6.67 (m, 1H), 4.67 (m, 1H), 2.32 (m, 4H), 2.19 (s, 3H), 1.89 (m, 5H), MS (EI): 553.3 (MH+).

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
customThe crude product was purified via reverse phase HPLC (aqueous ammonium acetate/acetonitrile)

Sources & evidence

ORD record: ord-dcbeafeb9a2846d69f2c0a6eafac924d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088767B2

Reaction notes

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