Trimethyl orthobeznoate → HCID 86672710, compound

HRID 2369912Notes

Reaction equation

HRID 2369912 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CO[C:21]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(OC)OC>C(O)(=O)C>[CH3:16][O:15][CH:14]([O:17][CH3:18])[CH2:13][N:12]1[C:3]2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=2[N:1]=[C:21]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 69720Trimethyl orthobeznoateHCID 66889618HCID 66889618, compound

Product 1

HCID 86672710HCID 86672710, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (922 mg, 3.6 mmol) from Step C of Example 13 was stirred in glacial acetic acid (2.5 mL) and (trimethoxymethyl)benzene (2.0 g, 10.9 mmol) at 70° C. for 3 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate) to give methyl 1-(2,2-dimethoxyethyl)-2-phenyl-1H-benzo[d]imidazole-7-carboxylate as a brown oil (1.0 g, 83%): 1H NMR (500 MHz, CDCl3) δ 7.99 (d, J=8.0 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.72-7.70 (m, 2H), 7.53-7.51 (m, 3H), 7.33 (t, J=8.0 Hz, 1H), 4.76 (d, J=5.0 Hz, 2H), 4.24 (t, J=5.0 Hz, 1H), 3.99 (s, 3H), 3.07 (s, 6H); MS (ESI+) m/z 341 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7f9151909d8f444f9047d1f1fd186dab
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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