Trifluoroacetic acid → HCID 86726703, compound

HRID 1499457Notes

Reaction equation

HRID 1499457 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C:16]1[S:20][C:19]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[N:18][C:17]=1[C:29]([NH:31][C:32]1[C:33]([N:43]2[CH2:48][CH2:47][CH2:46][C@H:45]([NH:49]C(=O)OC(C)(C)C)[CH2:44]2)=[C:34]2[CH2:40][CH2:39][C:38]([OH:42])([CH3:41])[C:35]2=[N:36][CH:37]=1)=[O:30])=O)(C)(C)C>C(Cl)Cl.CO.[NH4+].[OH-]>[NH2:15][C:16]1[S:20][C:19]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[N:18][C:17]=1[C:29]([NH:31][C:32]1[C:33]([N:43]2[CH2:48][CH2:47][CH2:46][C@H:45]([NH2:49])[CH2:44]2)=[C:34]2[CH2:40][CH2:39][C:38]([OH:42])([CH3:41])[C:35]2=[N:36][CH:37]=1)=[O:30]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726702HCID 86726702, compound

Product 1

HCID 86726703HCID 86726703, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Procedure

TFA (0.02 mL, 0.2 mmol) was added to a solution of tert-butyl {(3S)-1-[3-({[5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)-7-hydroxy-7-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]piperidin-3-yl}carbamate (4.0 mg, 0.0044 mmol) in DCM (0.01 mL). The reaction mixture was stirred at room temperature for 30 min., and then diluted with MeOH and neutralized with NH4OH. After filtration, the crude was purified by preparative LC-MS (Waters SunFire™ preparative C18 5 μm 30×10 mm column, flow rate 60 mL/min., eluting with a gradient of MeCN and water with 0.1% TFA) to give the title compound tris-trifluoroacetate salt as two diastereoisomers.

Workup

  1. filtrationAfter filtration
  2. customthe crude was purified by preparative LC-MS (Waters SunFire™ preparative C18 5 μm 30×10 mm column, flow rate 60 mL/min.
  3. washeluting with a gradient of MeCN and water with 0.1% TFA)

Sources & evidence

ORD record
ord-e86d2e0290254bdfbf0addce79d588db
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

Loading…