Hydrochloric Acid → HCID 178502265, compound

HRID 1257692Notes

Reaction equation

HRID 1257692 reaction equation
[CH3:1][O:2][C:3](=[O:31])[NH:4][C@H:5]1[CH2:9][CH2:8][C@H:7]([N:10]2[C:21]3[C:13](=[CH:14][N:15]=[C:16]4[C:20]=3[CH:19]=[CH:18][N:17]4S(C3C=CC=CC=3)(=O)=O)[N:12]=[N:11]2)[CH2:6]1.[OH-].[Na+].Cl>CO.C1COCC1>[CH3:1][O:2][C:3](=[O:31])[NH:4][C@H:5]1[CH2:9][CH2:8][C@H:7]([N:10]2[C:21]3[C:13](=[CH:14][N:15]=[C:16]4[C:20]=3[CH:19]=[CH:18][NH:17]4)[N:12]=[N:11]2)[CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131730644racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid methyl ester

Product 1

HCID 178502265HCID 178502265, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid methyl ester (171 mg, 380 μmol) in methanol (2 mL) and THF (1 mL) was treated with a 1M sodium hydroxide solution (2 mL) and stirred at ambient temperature for 1.5 hours. Dilute HCl was added and the mixture purified by Isolute® SCX-2 column (gradient: methanol to 2M NH3 in methanol solution). The residue obtained was purified further by column chromatography on silica gel (gradient: 50% ethyl acetate in cyclohexane then 0-10% methanol in ethyl acetate). The product was further purified by a diethyl ether/cyclohexane trituration to afford 48 mg (41%) of racemic trans [3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid methyl ester as a white solid. LCMS (Method A, ESI): RT=2.92 min, m+H=301.3; 1H NMR (400 MHz, DMSO) δ: 12.35 (s, 1H), 8.99 (s, 1H), 7.60 (d, 1H), 7.47 (d, 1H), 7.03 (d, 1H), 5.66 (m, 1H), 4.28 (m, 1H), 3.55 (s, 3H), 2.50 (m, 2H), 2.23 (m, 3H), 1.73 (m, 1H).

Workup

  1. customthe mixture purified by Isolute® SCX-2 column (gradient: methanol to 2M NH3 in methanol solution)
  2. customThe residue obtained
  3. customwas purified further by column chromatography on silica gel (gradient
  4. customThe product was further purified by a diethyl ether/cyclohexane trituration

Sources & evidence

ORD record
ord-d2760ec6c8ad4c08b04a1d0c6a142a4a
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

Loading…