Sodium Hydroxide → 2-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

HRID 69412Notes

Reaction equation

HRID 69412 reaction equation
[CH3:1][N:2]([CH3:28])[C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24]C)[CH:20]=4)[C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4]1.[OH-].[Na+]>Br>[CH3:1][N:2]([CH3:28])[C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=4)[C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 689879542-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-6-methoxy-3,4-dihydro-2H-isoquinolin-1-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-6-methoxy-3,4-dihydro-2H-isoquinolin-1-one (9.3 g) and hydrogen bromide (48% strength in water; 140 mL) was heated at 100° C. for 12 hours. The cooled reaction solution was adjusted to pH 10 with sodium hydroxide solution (4N). The precipitate was filtered off with suction, washed with water until neutral and dried. The product with the molecular weight of 369.44 (C21H24FN3O2) was obtained in this way; MS (ESI): 370 (M+H+).

Workup

  1. customThe cooled reaction solution
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed with water until neutral and
  4. customdried
  5. customThe product with the molecular weight of 369.44 (C21H24FN3O2) was obtained in this way

Sources & evidence

ORD record
ord-0fc20ac2c442475f8017d300cf77de2e
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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