Trifluoroacetic acid → HCID 117871497, compound

HRID 627021Notes

Reaction equation

HRID 627021 reaction equation
[CH:1]1([C@H:7]([NH:28]C(=O)OC(C)(C)C)[C:8](=[O:27])[N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11][C@@H:10]2[C:18](=[O:26])[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:20]1([NH:19][C:18]([C@@H:10]2[N:9]([C:8](=[O:27])[C@@H:7]([NH2:28])[CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11]2)=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735249HCID 131735249, compound

Product 1

HCID 117871497HCID 117871497, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

For Intermediate 4: In a 100 mL round-bottomed flask, tert-butyl (R)-(1S)-1-cyclohexyl-2-oxo-2-(2-(phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)ethylcarbamate (100 mg, 209 μmol, Eq: 1.00) was combined with DCM (2 mL) to give a colorless solution. TFA (2 mL, 26.0 mmol, Eq: 124) was added and the reaction was stirred for 1 h. The crude reaction mixture was concentrated in vacuo. The residue was dissolved in DCM (20 mL) and washed with saturated aqueous NaHCO3 (5 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give (R)-1-((S)-2-amino-2-cyclohexyl-acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid phenylamide as a white solid (56 mg), m/z=379 (M+H).

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was dissolved in DCM (20 mL)
  5. washwashed with saturated aqueous NaHCO3 (5 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32e0c00cf9f841b6bdf540f8c3cbfca4
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

Loading…