Dichloromethane → HCID 178449459, compound

HRID 242357Notes

Reaction equation

HRID 242357 reaction equation
C(OC([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][C:16](=[O:22])[NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])[N:10]=[C:9]1[NH2:23])=O)(C)(C)C.C(O)(C(F)(F)F)=O.[Cl:31]CCl>>[ClH:31].[NH2:23][C:9]1[NH:8][CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][C:16]([NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:22])[N:10]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67061977HCID 67061977, compound

Product 1

HCID 178449459HCID 178449459, compoundYield 97%

Procedure

A solution of 2-amino-4-(3-isobutylcarbamoyl-propyl)-imidazole-1-carboxylic acid tert-butyl ester 23 (76 mg, 0.234 mmol) in anhydrous dichloromethane (1 mL) was cooled to 0° C. TFA (1 mL) was charged into the flask and the reaction stirred for 5 h. After that time the reaction was evaporated to dryness and toluene (2 mL) was added. Again the mixture was concentrated and the process repeated. The resulting TFA salt was dissolved in dichloromethane (1 mL) and 2M HCl in diethyl ether (0.50 mL) was added followed by cold diethyl ether (8 mL). The precipitate was collected by filtration and washed with diethyl ether (3 mL) to yield the target compound 8 (59 mg, 97%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 12.14 (s, 1H), 11.70 (s, 1H), 7.89 (m, 1H), 7.34 (br s, 2H), 6.55 (s, 1H), 2.84 (t, 211, J=6.6 Hz), 2.38 (t, 211, J=7.5 Hz), 2.10 (t, 2H, J=7.5 Hz), 1.60-1.79 (m, 3H), 0.82 (d, 6H, J=6.3 Hz); 13C NMR (75 MHz, DMSO-d6) δ 171.52, 146.78, 126.31, 108.68, 46.00, 34.41, 28.09, 23.94, 23.64, 20.18; HRMS (ESI) calcd for C11H21N4O (MH)+ 225.1709, found 225.1711.

Workup

  1. customAfter that time the reaction was evaporated to dryness and toluene (2 mL)
  2. additionwas added
  3. concentrationAgain the mixture was concentrated
  4. dissolutionThe resulting TFA salt was dissolved in dichloromethane (1 mL)
  5. addition2M HCl in diethyl ether (0.50 mL) was added
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with diethyl ether (3 mL)

Sources & evidence

ORD record
ord-2ff5db58de344b9c8cd90c06053b4116
Source dataset
uspto-grants-2014_02
Patent number
US08653124B2

Reaction notes

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