Methyl chloroformate → racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid methyl ester

HRID 1257691Notes

Reaction equation

HRID 1257691 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[C:6]1([S:12]([N:15]2[CH:26]=[CH:25][C:24]3[C:16]2=[N:17][CH:18]=[C:19]2[C:23]=3[N:22]([C@H:27]3[CH2:31][CH2:30][C@H:29]([NH2:32])[CH2:28]3)[N:21]=[N:20]2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:5][O:4][C:2](=[O:3])[NH:32][C@H:29]1[CH2:30][CH2:31][C@H:27]([N:22]2[C:23]3[C:19](=[CH:18][N:17]=[C:16]4[C:24]=3[CH:25]=[CH:26][N:15]4[S:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)(=[O:14])=[O:13])[N:20]=[N:21]2)[CH2:28]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 131730643racemic trans 3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamine

Product 1

HCID 131730644racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid methyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (31.0 μL, 0.40 mmol) was added to a stirred mixture of racemic trans 3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamine (150 mg, 390 μmol) and diisopropylethylamine (135 μL, 790 μmol) in DCM (3 mL) at ambient temperature. Stirring was continued for 4 hours. The mixture was concentrated under vacuum and the residue obtained purified by column chromatography on silica gel (gradient: 0 to 100% ethyl acetate in pentane) to afford 171 mg (98%) of racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid methyl ester as a colourless foam. LCMS (Method B, ESI): RT=3.48 min, m+H=441.3.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue obtained
  3. custompurified by column chromatography on silica gel (gradient: 0 to 100% ethyl acetate in pentane)

Sources & evidence

ORD record
ord-603ec870918d4b54a8b397d1ab224591
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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