Cesium carbonate → 4-(2-Methoxy-4-{1-oxo-6-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-1H-isoquinolin-2-yl}-phenyl)-[1,4]diazepane-1-carboxylic acid 3-fluoro-propyl ester

HRID 69517Notes

Reaction equation

HRID 69517 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][O:27]5)[CH:20]=4)[C:15]3=[O:31])=[CH:10][C:9]=2[O:32][CH3:33])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:35][CH2:36][CH2:37][F:38].[C:39](=O)([O-:41])[O-:40].[Cs+].[Cs+]>CN(C=O)C>[F:38][CH2:37][CH2:36][CH2:35][O:41][C:39]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][O:27]5)[CH:20]=4)[C:15]3=[O:31])=[CH:10][C:9]=2[O:32][CH3:33])[CH2:2][CH2:3]1)=[O:40]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 689913772-(4-[1,4]Diazepan-1-yl-3-methoxy-phenyl)-6-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-2H-isoquinolin-1-one

Product 1

HCID 579167194-(2-Methoxy-4-{1-oxo-6-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-1H-isoquinolin-2-yl}-phenyl)-[1,4]diazepane-1-carboxylic acid 3-fluoro-propyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-[1,4]Diazepan-1-yl-3-methoxy-phenyl)-6-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-2H-isoquinolin-1-one (50 mg) and 1-Bromo-3-fluoro-propane (18 mg) in DMF (1 mL) was added cesium carbonate (54 mg) and the mixture was stirred overnight. The crude mixture was purified by preparative HPLC. The product with the molecular weight of 553.64 (C30H36FN3O6) was obtained in this way; MS (ESI): 554 (M+H+).

Workup

  1. customThe crude mixture was purified by preparative HPLC
  2. customThe product with the molecular weight of 553.64 (C30H36FN3O6) was obtained in this way

Sources & evidence

ORD record
ord-5f99bf5486a64320862b253200e73e5d
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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