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Sodium Thiosulfate → 2-[4-(1,4-Dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-methoxy-2H-isoquinolin-1-one

HRID 69482
Notes
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Reaction equation

HRID 69482 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O:23]1[C:27]2([CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:51])[C:40]4[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:41]=4[CH2:48][CH2:49]O)=[CH:34][C:33]=3[F:52])[CH2:28]2)[O:26][CH2:25][CH2:24]1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[O:26]1[C:27]2([CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][C:35]([N:38]4[CH:49]=[CH:48][C:41]5[C:40](=[CH:45][CH:44]=[C:43]([O:46][CH3:47])[CH:42]=5)[C:39]4=[O:51])=[CH:34][C:33]=3[F:52])[CH2:28]2)[O:23][CH2:24][CH2:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2×HCID 68989883N-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-2-(2-hydroxyethyl)-4-methoxy-benzamide

Product 1

HCID 689902272-[4-(1,4-Dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-methoxy-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Dess-Martin periodinane (7 g) was added to a solution of N-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-2-(2-hydroxyethyl)-4-methoxy-benzamide (4.6 g) in methylene chloride (279 mL). The reaction mixture was stirred for 2 h at room temperature, then further Dess-Martin periodinane (1.4 g) was added, stirring for a further 4 h at room temperature. Then 5% Na2S2O3 solution was added to the reaction solution and the organic phase was then washed with water. The methylene chloride phase was dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 396.15 (C22H21FN2O4); MS (ESI): 397 (M+H+).

Workup

  1. stirringstirring for a further 4 h at room temperature
  2. washthe organic phase was then washed with water
  3. dry with materialThe methylene chloride phase was dried over sodium sulfate
  4. customthe solvent was removed in vacuum
  5. customThe raw product was purified by preparative HPLC
  6. customIn this way the product was obtained with molecular weight 396.15 (C22H21FN2O4)

Sources & evidence

ORD record
ord-aa94c331bfbc44178c5186fc0abceb12
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822495B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes