HCID 56953688, compound → HCID 178511835, compound

HRID 1630078Notes

Reaction equation

HRID 1630078 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17](=O)[C@@H:18]([NH:28]C(=O)OC(C)(C)C)[CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(=O)C>[CH2:21]([O:20][CH2:19][C@@H:18]([C:17]1[NH:16][C:3]2[CH:4]=[CH:5][C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)=[CH:7][C:2]=2[N:1]=1)[NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 56953688HCID 56953688, compound

Product 1

HCID 178511835HCID 178511835, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (S)-tert-butyl 1-(2-amino-4-(4-fluorophenoxy)phenylamino)-3-(benzyloxy)-1-oxopropan-2-ylcarbamate (610 mg, 1.23 mmol) and acetic acid (6 mL) was stirred at 60° C. for 1 hour. The acetic acid was remove under vacuum and the residue was dissolve in hydrogen chloride (4 mL, 4N in dioxane). The resulting solution was stirred at ambient temperature for 30 minutes and then concentration. Product was purified from the residue by PrepLC to give (R)-2-(benzyloxy)-1-(5-(4-fluorophenoxy)-1H-benzo[d]imidazol-2-yl)ethanamine (250 mg, 54%) as a pale yellow foam.

Workup

  1. customThe acetic acid was remove under vacuum
  2. dissolutionthe residue was dissolve in hydrogen chloride (4 mL, 4N in dioxane)
  3. stirringThe resulting solution was stirred at ambient temperature for 30 minutes
  4. concentrationconcentration
  5. customProduct was purified from the residue by PrepLC

Sources & evidence

ORD record
ord-ec41837a624f4d59a1473dede87f7872
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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