Ethyl orthoformate → HCID 73670274, compound

HRID 2284581Notes

Reaction equation

HRID 2284581 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]([N+:29]([O-])=O)=[C:18]([NH:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:32].[CH:33](OCC)(OCC)OCC>Cl.CC(N(C)C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]4[N:29]=[CH:33][N:20]([CH2:21][CH2:22][N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)[C:18]=4[CH:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:32]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 86715489HCID 86715489, compound

Product 1

HCID 73670274HCID 73670274, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
65 °C

Procedure

The above residue containing 5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-N-(2-morpholinoethyl)-2-nitrobenzenamine was added DMA (1 mL), triethyl orthoformate (250 uL) and treated with one drop of concentrated HCl. The homogeneous solution was heated at 65° C. for 15 hours in a sealed vial. The reaction was cooled and the volatiles were removed with a stream of nitrogen gas. The residue was triturated with aq. NaHCO3, resulting solid collected by filtration and purified by HPLC to yield 25 mg of the desired product 6-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-1-(2-morpholino ethyl)-1H-benzo[d]imidazole. 1H NMR (DMSO-d6): δ 8.58 (dd, J=4.7, 1.6 Hz, 1H), 8.15 (s, 1H), 7.84 (dd, J=7.8, 1.6 Hz, 1H), 7.56 (d, J=8.3 Hz, 1H), 7.43 (dd, J=7.8, 4.7 Hz, 1H), 7.28 (d, J=4.8 Hz, 2H), 7.05 (dd, J=8.3, 1.5 Hz, 1H), 7.03-6.75 (m, 2H), 4.19 (t, J=6.4 Hz, 2H), 3.55-3.36 (m, 4H), 2.44-2.15 (m, 6H), 2.06 (s, 3H). MS (m/e): 417 (MH+).

Workup

  1. temperatureThe reaction was cooled
  2. customthe volatiles were removed with a stream of nitrogen gas
  3. customThe residue was triturated with aq. NaHCO3
  4. customresulting solid
  5. filtrationcollected by filtration
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-97bc472f671d4a67b1895aa6ad314b67
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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