Water → (S)-4-(2-amino-5-bromopyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide

HRID 595942Notes

Reaction equation

HRID 595942 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([F:17])[CH:9]=2)=[CH:6][C:5]([Br:18])=[CH:4][N:3]=1.[NH2:19][C@@H:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)[CH2:21][OH:22].O.CCOC(C)=O>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH:19][C@@H:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[CH2:21][OH:22])=[O:14])=[C:10]([F:17])[CH:9]=2)=[CH:6][C:5]([Br:18])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 59694427(S)-2-amino-2-(3-chlorophenyl)ethanolHCID 1180467884-(2-Amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid

Product 1

HCID 118046407(S)-4-(2-amino-5-bromopyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid (300 mg, 0.964 mmol) in THF (8.036 mL) was added (S)-2-amino-2-(3-chlorophenyl)ethanol (331 mg, 1.157 mmol). The reaction mixture was stirred for 15 h. After water was added, the reaction mixture was worked up with EtOAc, the organic layer was dried over anhydrous Na2SO4, filtered off and concentrated in vacuo. The crude (S)-4-(2-amino-5-bromopyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide was used for the next step without further purification. LCMS (m/z): 464.1/466.1 (MH+), 0.69 min.

Workup

  1. dry with materialthe organic layer was dried over anhydrous Na2SO4
  2. filtrationfiltered off
  3. concentrationconcentrated in vacuo
  4. customThe crude (S)-4-(2-amino-5-bromopyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide was used for the next step without further purification
  5. custom464.1/466.1 (MH+), 0.69 min.

Sources & evidence

ORD record
ord-7a028974886b4cff8ba4e7a4d3512b0e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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