HCID 58459330, compound → HCID 178461854, compound

HRID 2036590Notes

Reaction equation

HRID 2036590 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=O)[C@@H:11]([NH:13]C(=O)OC(C)(C)C)[CH3:12]>CC(O)=O>[F:8][C:7]1[C:2]2[NH:1][C:10]([C@@H:11]([NH2:13])[CH3:12])=[N:9][C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 58459330HCID 58459330, compound

Product 1

HCID 178461854HCID 178461854, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of (S)-tert-butyl 1-(2-amino-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate (2.08 g, 7.00 mmol) in AcOH (30 mL) was heated at 65° C. for 2 h, cooled to rt. After being concentrated under reduced pressure, the residue was subjected to 4 M HCl in 1,4-Dioxane (20 mL). The resultant mixture was stirred at rt for 40 min. The mixture was concentrated under reduced pressure and dissolved in water (10 mL) and then basified with 1 N NaOH to pH 9.5. The mixture was concentrated under reduced pressure. The residue was triturated with MeOH-DCM (1:1). The crude product was purified by column chromatography on a silica gel column using DCM-MeOH—NH4OH (9:1:0.05) as eluent to give (S)-1-(7-fluoro-1H-benzo[d]imidazol-2-yl)ethanamine: LC-MS (ESI) m/z 180.1 [M+H]+.

Workup

  1. concentrationAfter being concentrated under reduced pressure
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutiondissolved in water (10 mL)
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customThe residue was triturated with MeOH-DCM (1:1)
  6. customThe crude product was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-c949e2d27362464db654be4e15ba81b5
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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