Trifluoroacetic acid → ethyl 5-(1-(4-amino-1H-indazol-1-yl)-1-(4-chlorophenyl)propyl)-1,2,4-oxadiazole-3-carboxylate

HRID 1427274Notes

Reaction equation

HRID 1427274 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:28]1[O:32][N:31]=[C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:29]=1)([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH2:19][CH3:20])=O)(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:28]1[O:32][N:31]=[C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:29]=1)([C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 68175868ethyl 5-(1-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-1-(4-chlorophenyl)propyl)-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 70563925ethyl 5-(1-(4-amino-1H-indazol-1-yl)-1-(4-chlorophenyl)propyl)-1,2,4-oxadiazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step C above (0.083 g, 0.16 mmol) and anisole (0.068 g, 0.63 mmol) in DCM (1.0 mL) was added TFA (0.18 g, 1.58 mmol). After stirred overnight at RT, the reaction mixture was concentrated to dryness under reduced pressure. The resulting residue was re-dissolved in a mixture of acetonitrile and water followed by addition of 1 N HCl aqueous solution (0.16 mL). The solution was dried in a lyophilized to give crude title compound. LC/MS m/z=426.1[M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionThe resulting residue was re-dissolved in a mixture of acetonitrile and water
  3. additionfollowed by addition of 1 N HCl aqueous solution (0.16 mL)
  4. customThe solution was dried in

Sources & evidence

ORD record
ord-7b2aece3729e419ca2edc451ffcfd143
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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