Acetic Acid → N-(1-(7-bromo-1-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide

HRID 2036666Notes

Reaction equation

HRID 2036666 reaction equation
[Br:1][C:2]1[C:3]([NH:21][C:22]2[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=2)=[C:4]([NH:8][C:9](=O)[C@@H:10]([NH:12][C:13](=O)[O:14]C(C)(C)C)[CH3:11])[CH:5]=[CH:6][CH:7]=1.[CH3:29]C(O)=O>>[Br:1][C:2]1[C:3]2[N:21]([C:22]3[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=3)[C:9]([CH:10]([NH:12][C:13](=[O:14])[CH3:29])[CH3:11])=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 58459349(S)-tert-butyl 1-(3-bromo-2-(5-fluoropyridin-3-ylamino)phenylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 58459399N-(1-(7-bromo-1-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide

Procedure

A solution of (S)-tert-butyl 1-(3-bromo-2-(5-fluoropyridin-3-ylamino)phenylamino)-1-oxopropan-2-ylcarbamate (2.4253 g, 5.35 mmol) in AcOH (17.83 mL) was heated at 100° C. with stirring. After 5 days, the mixture was removed from the heat and poured into a biphase of DCM (100 mL) and satd. sodium bicarbonate solution (100 mL). The mixture was basified with 10N NaOH (10 mL). The organic layer was washed with water (100 mL×3) and brine (100 mL X1), dried over MgSO4, filtered, and concentrated in vacuo to provide N-(1-(7-bromo-1-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide as a dark brown solid: LC-MS (ESI) m/z 376.9 [M+H (79Br)]+ and 379 [M+H (81Br)]+.

Workup

  1. customthe mixture was removed from the
  2. temperatureheat
  3. additionpoured into a biphase of DCM (100 mL)
  4. washThe organic layer was washed with water (100 mL×3) and brine (100 mL X1)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fb02422057a46bb8f87e8d83d38803a
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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