Trifluoroacetic acid → Trifluoroacetic acid

HRID 596125Notes

Reaction equation

HRID 596125 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C(C)(C)C)=[O:15])=[C:10]([F:21])[CH:9]=1.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[C:10]([F:21])[CH:9]=2)=[N:6][C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:4][N:3]=1.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118045523Ethyl 5-amino-6-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyrazine-2-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 1180454784-(3-Amino-6-(ethoxycarbonyl)pyrazin-2-yl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-amino-6-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyrazine-2-carboxylate (0.253 g, 0.7 mmol) in DCM (4 mL) at RT was added TFA (2.157 mL, 28.0 mmol). The resultant solution was stirred at RT for 2 hours. The reaction solution was concentrated and further dried to afford the crude desired product as a TFA salt. This product was directly used at the next step. 0.214 g (100% yield) of light sticky liquid was obtained. LC-MS (m/z): 306.1 (MH+), 0.563 min.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customfurther dried

Sources & evidence

ORD record
ord-0c47be53fa834000a1fc0252da94384e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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