Trifluoroacetic acid → HCID 73603910, compound

HRID 627054Notes

Reaction equation

HRID 627054 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]([CH:12]1[N:20]([C:21](=[O:43])[C@@H:22]([NH:29][C:30](=[O:42])[C@@H:31]([N:33](C)[C:34](=O)OC(C)(C)C)[CH3:32])[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[NH:9][C:10]([C@H:12]1[N:20]([C:21](=[O:43])[C@@H:22]([NH:29][C:30](=[O:42])[C@@H:31]([NH:33][CH3:34])[CH3:32])[CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735270HCID 131735270, compound

Product 1

HCID 73603910HCID 73603910, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2S)-1-((1S)-2-(2-(2,6-difluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-oxo-1-(tetrahydropyran-4-yl)ethylamino)-1-oxopropan-2-yl(methyl)carbamate (54 mg, 89.8 μmol, Eq: 1.00) in DCM (1 mL) was added TFA (1 mL, 13.0 mmol, Eq: 145) and the resulting solution was stirred at rt for 1 h. The reaction mixture was concentrated in vacuo and the residue was treated with saturated aqueous NaHCO3 (10 mL). The resulting mixture was extracted with DCM (2×10 mL), the combined organic layers dried over Na2SO4, and then concentrated in vacuo. Treatment of the residue with diethyl ether/hexanes gave (S)-1-[(S)-2-((S)-2-methylamino-propionylamino)-2-(tetrahydropyran-4-yl)-acetyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2,6-difluoro-phenyl)-amide as a white solid (45 mg), m/z=502 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe resulting mixture was extracted with DCM (2×10 mL)
  4. dry with materialthe combined organic layers dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1534a108185d40fcb8af2fe304f5c06a
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

Loading…