Hydrazine hydrate (1:1) → HCID 178432049, compound

HRID 539172Notes

Reaction equation

O.[NH2:2]N.[Cl:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][N:13]1[C:17]2[CH:18]=[C:19]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH:20]=[C:21]([C:22](/[N:24]=[CH:25]/[N:26](C)C)=O)[C:16]=2[N:15]=[C:14]1[CH3:35].C([O-])(O)=O.[Na+]>C(O)(=O)C>[Cl:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][N:13]1[C:17]2[CH:18]=[C:19]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[CH:20]=[C:21]([C:22]3[N:24]=[CH:25][NH:26][N:2]=3)[C:16]=2[N:15]=[C:14]1[CH3:35]

Participants

Conditions

Temperature: 130 °C

Procedure

Hydrazine monohydrate (2 mL) was added to a solution of 1-[(2,3-dichlorophenyl)methyl]-N-[(1E)-(dimethylamino)methylidene]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxamide (220 mg, 0.46 mmol) in acetic acid (5 mL) and stirred at 130° C. for 20 min. The reaction mixture was cooled to rt and poured into saturated NaHCO3 solution (15 mL). The mixture was extracted with DCM (30 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography eluted with DCM:MeOH=30:1 to give the desired product (110 mg, 53%), as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.50 (s, 3H), 3.12 (t, 4H, J=4.8 Hz), 3.75 (t, 4H, J=4.8 Hz), 5.62 (s, 2H), 6.36 (d, 1H, J=8.1 Hz), 7.21 (s, 1H), 7.27 (t, 1H, J=8.1 Hz), 7.54 (s, 1H), 7.61 (d, 1H, J=8.1 Hz), 8.08 (s, 1H), 13.80 (s, 1H); LC-MS: m/e=443 [M+1]+.

Workup

temperatureThe reaction mixture was cooled to rt
extractionThe mixture was extracted with DCM (30 mL×3)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified by silica gel chromatography
washeluted with DCM

Sources & evidence

ORD record: ord-377cee15f015441b8b7523f571c42c25
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865912B2

Reaction notes

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