Acetic Acid → HCID 90052266, compound

HRID 2284727Notes

Reaction equation

HRID 2284727 reaction equation
[C:1]([NH:8][CH2:9][C:10](O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[I:13][C:14]1[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=1.C(O)(=O)C.O>O1CCCC1.ClC(OCC(C)C)=O.CN1CCOCC1.C(OCC)(=O)C>[I:13][C:14]1[CH:19]=[CH:18][C:17]2[N:20]=[C:10]([CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH:21][C:16]=2[CH:15]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 78288N-(tert-butoxycarbonyl)glycineHCID 112070494-Iodobenzene-1,2-diamine

Product 1

HCID 90052266HCID 90052266, compoundYield 78.6%

Reagents, catalysts & solvents 4

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 62365Isobutyl chloroformateSolvent

Procedure

To a solution of N-Boc-glycine (129 mg) in tetrahydrofuran (3.5 mL), isobutyl chloroformate (97 μL) and N-methylmorpholine (81 μL) were added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture, 4-iodobenzene-1,2-diamine (200 mg) synthesized according to the method described in WO2010/065668 A1 was added under ice cooling, and the mixture was stirred at room temperature for 1 hour, and then acetic acid (3.5 mL) was added, and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 80 to 0% hexane in ethyl acetate) to obtain tert-butyl ((6-iodo-1H-benzo[d]imidazol-2-yl)methyl)carbamate (G4, 216 mg).

Workup

  1. additionwas added under ice cooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. stirringthe mixture was stirred at 70° C. for 2 hours
  4. customThe organic layer was separated
  5. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluent, 80 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-34d64255e62846c5bce3e0374314337e
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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