Pyridine → Trifluoromethanesulfonic acid 2-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl ester

HRID 69414Notes

Reaction equation

HRID 69414 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][N:17]([CH3:42])[C@@H:18]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:38][CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[C:34](O)[CH:35]=4)[C:30]3=[O:40])=[CH:25][C:24]=2[F:41])[CH2:19]1.N1C=CC=CC=1>ClCCl>[CH3:16][N:17]([CH3:42])[C@@H:18]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:38][CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[C:34]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:35]=4)[C:30]3=[O:40])=[CH:25][C:24]=2[F:41])[CH2:19]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 689879832-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 86635103Trifluoromethanesulfonic acid 2-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (2.06 g) was added to a solution of 2-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (1.5 g) and pyridine (0.64 g) in dichloromethane (40 mL) at 0° C. After 30 minutes, the mixture was partitioned between water and dichloromethane, and the organic phase was dried over magnesium sulfate and concentrated. The product with the molecular weight of 501.50 (C22H23F4N3O4S) was obtained in this way; MS (ESI): 502 (M+H+).

Workup

  1. customthe mixture was partitioned between water and dichloromethane
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product with the molecular weight of 501.50 (C22H23F4N3O4S) was obtained in this way

Sources & evidence

ORD record
ord-8fd779e262d64cf6a87395e16586258a
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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