Trifluoroacetic acid → (5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propylsulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl dihydrogen phosphate

HRID 1056589Notes

Reaction equation

HRID 1056589 reaction equation
[P:1]([O-:47])([O-:46])([O:3][C:4](C(C)(C)C)(C(C)(C)C)[N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:13]=[C:8]2[C:7]([C:21](=[O:37])[C:22]2[C:27]([F:28])=[CH:26][CH:25]=[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[C:23]=2[F:36])=[CH:6]1)=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[P:1]([OH:46])([OH:47])([O:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:13]=[C:8]2[C:7]([C:21](=[O:37])[C:22]2[C:27]([F:28])=[CH:26][CH:25]=[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[C:23]=2[F:36])=[CH:6]1)=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86711103HCID 86711103, compound

Product 1

HCID 73388277(5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propylsulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl dihydrogen phosphateYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di-tert-butyl((5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propyl sulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl) phosphate (1 g, 1.4 mmol) in DCM (25 mL) was added TFA (1.6 mL, 2.4 g, 21 mmol). The reaction was stirred at rt for 2 h, and then concentrated in vacuo. The residue was washed with 20 mL of EtOAc to give the title compound as a white solid (0.56 g, 66.5%). The title compound was characterized by LC-MS and 1H NMR as shown below:

Workup

  1. concentrationconcentrated in vacuo
  2. washThe residue was washed with 20 mL of EtOAc

Sources & evidence

ORD record
ord-f2f265035e7645a1bf78f6750d906d8c
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

Loading…