Trifluoroacetic acid → HCID 86726667, compound

HRID 1499414Notes

Reaction equation

HRID 1499414 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[S:32][CH:31]=[CH: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[CH:30]=[CH:31][S:32][C:26]=23)[CH2:34]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726666HCID 86726666, compound

Product 1

HCID 86726667HCID 86726667, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.0 mL) was added to a solution of tert-butyl {(3S)-1-[6-({[2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)thieno[3,2-b]pyridin-7-yl]piperidin-3-yl}carbamate (92.2 mg, 0.161 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 (43.9 mg, 58%). 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 0.15% NH4OH, at flow rate of 30 mL/min.)

Sources & evidence

ORD record
ord-79449aebb044464f8c03ab19771d297e
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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