Methanol → HCID 58052373, compound

HRID 2190174Notes

Reaction equation

HRID 2190174 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:23])[CH2:15][CH2:16][CH2:17][N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:4].CNC(C1C2C=C3C(C)=CCCN(S(C)(=O)=O)C3=NC=2OC=1C1C=CC(F)=CC=1)=O.CO>[OH-].[OH-].[Pd+2].CCOC(C)=O>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[CH:14]([CH3:23])[CH2:15][CH2:16][CH2:17][N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 58052304HCID 58052304, compoundHCID 66663321HCID 66663321, compound

Product 1

HCID 58052373HCID 58052373, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methylene-6,7,8,9-tetrahydro-5H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide and 2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide (15 mg), Pd(OH)2 (20% on carbon, 4.9 mg), MeOH (0.56 ml) and EtOAc (0.14 ml) was stirred under hydrogen for 1.5 h at rt. The mixture was filtered through a 0.2 μM PTFE syringe filter and concentrated to give the title compound as an off-white solid. MS (ESI) m/z 432.3 (M+1). Retention time=1.23 min (Method A). 1H-NMR (400 MHz, CDCl3) δ ppm 8.13 (s, 1H), 7.94-7.86 (m, 2H), 7.31-7.23 (m, 2H), 5.88 (br, 1H), 3.51 (s, 3H), 3.39-3.31 (m, 1H), 2.10-1.62 (m, 6H), 1.49 (d, 3H).

Workup

  1. filtrationThe mixture was filtered through a 0.2 μM PTFE syringe
  2. filtrationfilter
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7896dbb2c2874df9a43d21eb2e6ccb83
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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