Methanol → HCID 178453992, compound

HRID 1257686Notes

Reaction equation

HRID 1257686 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:24]3[C:16](=[CH:17][N:18]=[C:19]4[C:23]=3[CH:22]=[CH:21][N:20]4S(C3C=CC=CC=3)(=O)=O)[N:15]=[N:14]2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO.C1COCC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:24]3[C:16](=[CH:17][N:18]=[C:19]4[C:23]=3[CH:22]=[CH:21][NH:20]4)[N:15]=[N:14]2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 131730637racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester

Product 1

HCID 178453992HCID 178453992, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester (2.00 g, 4.14 mmol), aqueous sodium hydroxide solution (10.4 mL, 20.7 mmol, 2M), methanol (30 mL) and THF (50 mL) was stirred at ambient temperature for 45 minutes. DCM was added and the solution washed (water and brine) and concentrated to dryness. Purification by column chromatography on silica gel (gradient: DCM to ethyl acetate) afforded 902 mg (64%) of racemic trans [3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester as an off white solid. LCMS (Method B, ESI): RT=3.21 min, m+H=343.3; 1H NMR (400 MHz, DMSO) δ: 12.34 (s, 1H), 8.99 (s, 1H), 7.60 (d, 1H), 7.18 (d, 1H), 7.03 (d, 1H), 5.64 (m, 1H), 4.23 (m, 1H), 2.47 (m, 2H, partially obscured by DMSO), 2.20 (m, 3H), 1.70 (m, 1H), 1.40 (s, 9H).

Workup

  1. washthe solution washed (water and brine)
  2. concentrationconcentrated to dryness
  3. customPurification by column chromatography on silica gel (gradient: DCM to ethyl acetate)

Sources & evidence

ORD record
ord-9c83f429a4594c6083096ddbba2b54f6
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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