Triethylamine → HCID 9839596, compound

HRID 432039Notes

Reaction equation

HRID 432039 reaction equation
Br.C(O[NH:7][CH:8]([CH3:20])[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19])(C)(C)C.C(N(CC)CC)C.[CH3:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>C(Cl)Cl>[NH2:7][CH:8]([CH3:20])[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH:19][C:33](=[O:34])[C:32]1[CH:36]=[CH:37][C:29]([CH3:28])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 18761808HCID 18761808, compound

Product 1

HCID 9839596HCID 9839596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-tert-butoxyaminopropyl)-2-aminobenzimidazole hydrobromide (1.00 g, 2.70 mmol) and triethylamine (1.9 mL, 3.79 mmol) in CH2Cl2 (50 mL) was added 4-methylbenzoyl chloride (0.46 g, 29.73 mmol) at 0° C. This mixture was stirred at 0° C. for 1 h and at room temperature overnight. The volatiles were evaporated and the residue was purified by flash chromatography using ethyl acetate-hexane (1:1). The fractions collected were concentrated in vacuo and the residue was dissolved in trifluoroacetic acid (5 ml) and stirred overnight. The trifluoroacetic acid was evaporated and the residue was dissolved in ethyl acetate and washed with a saturated solution of bicarbonate. Ethyl acetate was evaporated and the residue was purified by flash chromatography using CH2Cl2-MeOH (9.5: 0.5). The oil recovered after evaporation of solvent was transformed to the hydrochloride salt. MS 308 (M+1). 1HNMR (DMSO): δ 1.3(d, 3H), 2.37 (s, CH3), 3.80 (m, 1H), 4.45 (m, 2H), 7.26 (m, 4H), 7.55 and 7.62 (2d, 2H), 8.15 (d, 2H), 11.61 (bs, NH).

Workup

  1. customThe volatiles were evaporated
  2. customthe residue was purified by flash chromatography
  3. customThe fractions collected
  4. concentrationwere concentrated in vacuo
  5. dissolutionthe residue was dissolved in trifluoroacetic acid (5 ml)
  6. stirringstirred overnight
  7. customThe trifluoroacetic acid was evaporated
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washwashed with a saturated solution of bicarbonate
  10. customEthyl acetate was evaporated
  11. customthe residue was purified by flash chromatography
  12. customThe oil recovered
  13. customafter evaporation of solvent

Sources & evidence

ORD record
ord-94d0964233944edd8f5922be2ab4bd9d
Source dataset
uspto-grants-2003_12
Patent number
US06660870B1

Reaction notes

Loading…