Trifluoroacetic acid → HCID 86726655, compound

HRID 1499400Notes

Reaction equation

HRID 1499400 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[C:16]1[S:17][CH:18]=[C:19]([C:21]([NH:23][C:24]2[CH:25]=[N:26][C:27]3[C:32]([C:33]=2[N:34]2[CH2:39][CH2:38][CH2:37][C@H:36]([NH:40]C(=O)OC(C)(C)C)[CH2:35]2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:22])[N:20]=1>C(Cl)Cl>[NH2:40][C@H:36]1[CH2:37][CH2:38][CH2:39][N:34]([C:33]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][C:24]=2[NH:23][C:21]([C:19]2[N:20]=[C:16]([C:10]3[C:11]([F:15])=[CH:12][CH:13]=[CH:14][C:9]=3[F:8])[S:17][CH:18]=2)=[O:22])[CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726654HCID 86726654, compound

Product 1

HCID 86726655HCID 86726655, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.0 mL) was added to a solution of tert-butyl {(3S)-1-[3-({[2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)quinolin-4-yl]piperidin-3-yl}carbamate (57.4 mg, 0.101 mmol) in DCM (2.0 mL). The mixture was stirred at room temperature for 30 min., and then concentrated under reduced pressure. The resulting residue was purified using RP-HPLC (XBridge™ C18 column, eluting with a gradient of MeCN/water containing 0.15% NH4OH, at flow rate of 30 mL/min.) to afford the title compound as a white solid (25.4 mg, 54%). LCMS calc. for C24H22F2N5OS (M+H)+: m/z=466.1. found 466.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified
  3. washeluting with a gradient of MeCN/water containing 0.15% NH4OH, at flow rate of 30 mL/min.)

Sources & evidence

ORD record
ord-6b0ff3e9b76c4528965eb07e5761563f
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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