Trifluoroacetic acid → HCID 86680410, compound

HRID 1023169Notes

Reaction equation

HRID 1023169 reaction equation
COC1C=CC(C[N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]4[CH2:20][CH:19]4[C:21]4[O:22][C:23]([NH:26][C:27]5[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=5)=[N:24][N:25]=4)=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:37])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:35][C:33]([F:34])([F:36])[C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:23]2[O:22][C:21]([C@@H:19]3[CH2:20][C@H:18]3[C:14]3[CH:13]=[C:12]4[C:17](=[CH:16][CH:15]=3)[NH:8][C:9](=[O:37])[CH:10]=[CH:11]4)=[N:25][N:24]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86680411HCID 86680411, compound

Product 1

HCID 86680410HCID 86680410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(4-methoxybenzyl)-6-(2-(5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-oxadiazol-2-yl)cyclopropyl)quinolin-2(1H)-one (35 mg, 0.065 mmol) in DCM (5 mL) was added TFA (0.5 mL, 6.49 mmol) and stirred at room temperature overnight. The solvent was concentrated to give a crude product, purified by preparative HPLC on a Sunfire C18 column (150×19, 5μ) using a gradient of 0-100% ACN in 0.1% TFA to give trans-6-(2-(5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-oxadiazol-2-yl)cyclopropyl)quinolin-2(1H)-one. 1H NMR 400 MHz, MeOD: δ 1.65-1.79 (m, 2H), 2.43-2.47 (m, 1H), 2.70-2.75 (m, 1H), 6.64 (d, J=9.20 Hz, 1H), 7.35 (d, J=8.80 Hz, 1H), 7.47 (dd, J=2.00, 8.60 Hz, 1H), 7.57 (d, J=1.60 Hz, 1H), 7.68 (dd, J=8.80, 23.20 Hz, 4H), 7.97 (d, J=9.20 Hz, 1H). LCMS, RT 1.869 min; LCMS (ES-API), m/z 412.11.

Workup

  1. concentrationThe solvent was concentrated
  2. customto give a crude product
  3. custompurified by preparative HPLC on a Sunfire C18 column (150×19, 5μ)

Sources & evidence

ORD record
ord-55fb55ac66f04ee7b3bc8905e397083b
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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