Hydrazine hydrate (1:1) → HCID 178428027, compound

HRID 1188813Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:9]=2[CH3:18])[C:5]2[CH:19]=[C:20]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:21]=[C:22]([C:23]([NH2:25])=O)[C:4]=2[N:3]=1.COC(OC)[N:35]([CH3:37])C.O.[NH2:41]N>C(O)(=O)C>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[C:9]=2[CH3:18])[C:5]2[CH:19]=[C:20]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:21]=[C:22]([C:23]3[N:35]=[CH:37][NH:41][N:25]=3)[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 2-methyl-1-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-1H-benzimidazole-4-carboxamide (0.52 g, 1.202 mmol) in N,N-dimethylformamide dimethyl acetal (30 mL, 224 mmol) was stirred at 105° C. for 2 hours and the reaction is complete. The reaction was concentrated under reduced pressure. To the crude material was added Acetic Acid (30 mL) and hydrazine monohydrate (0.264 mL, 8.42 mmol). The reaction mixture was stirred at 100° C. for 1 h and concentrated. The crude was purified using silica gel (0˜2% MeOH/DCM) to give the product (0.245 g, 42%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.48 (s, 3H), 2.56 (s, 3H), 3.10-3.15 (m, 4H), 3.67-3.79 (m, 4H), 5.62 (s, 2H), 6.37 (d, J=7.83 Hz, 1H), 7.19 (d, J=2.02 Hz, 1H), 7.26 (t, J=7.83 Hz, 1H), 7.55 (d, J=1.77 Hz, 1H), 7.62 (d, J=7.58 Hz, 1H), 8.09 (s, 1H), 13.83 (s, 1H). MS (ES+) m/e 457.1[M+H]+.

Workup

concentrationThe reaction was concentrated under reduced pressure
stirringThe reaction mixture was stirred at 100° C. for 1 h
concentrationconcentrated
customThe crude was purified

Sources & evidence

ORD record: ord-ff797dd888f54e479d1ba5d4bbfc7472
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674090B2

Reaction notes

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