Trifluoroacetic acid → HCID 86726661, compound

HRID 1499407Notes

Reaction equation

HRID 1499407 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[C:25]([N:33]3[CH2:38][CH2:37][CH2:36][C@H:35]([NH:39]C(=O)OC(C)(C)C)[CH2:34]3)=[C:26]3[CH:32]=[CH:31][S:30][C:27]3=[N:28][CH:29]=2)=[O:22])[N:20]=1>C(Cl)Cl>[NH2:39][C@H:35]1[CH2:36][CH2:37][CH2:38][N:33]([C:25]2[C:24]([NH:23][C:21]([C:19]3[N:20]=[C:16]([C:10]4[C:9]([F:8])=[CH:14][CH:13]=[CH:12][C:11]=4[F:15])[S:17][CH:18]=3)=[O:22])=[CH:29][N:28]=[C:27]3[S:30][CH:31]=[CH:32][C:26]=23)[CH2:34]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726660HCID 86726660, compound

Product 1

HCID 86726661HCID 86726661, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.0 mL) was added to a solution of tert-butyl {(3S)-1-[5-({[2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)thieno[2,3-b]pyridin-4-yl]piperidin-3-yl}carbamate (118.2 mg, 0.2068 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 0.1% NH4OH, at flow rate of 30 mL/min.) to afford the title compound as a white solid (33.5 mg, 34%). LCMS calc. for C22H20F2N5OS2 (M+H)+: m/z=472.1. found 472.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified
  3. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at flow rate of 30 mL/min.)

Sources & evidence

ORD record
ord-8ea88c4f979d46599315ce55b4494924
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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