Tetrahydrofuran → HCID 131726154, compound

HRID 857427Notes

Reaction equation

HRID 857427 reaction equation
[CH3:1][CH:2]([CH:6]1[C:10]2=[C:11]([S:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:12]3[C:13]([CH:23]([CH3:25])[CH3:24])=[CH:14][C:15]([C:18]4[N:19]=[N:20][NH:21][N:22]=4)=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1)[C:3]([O-:5])=[O:4].[CH2:34]1COCC1>>[CH3:1][CH:2]([CH:6]1[C:10]2=[C:11]([S:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:12]3[C:13]([CH:23]([CH3:24])[CH3:25])=[CH:14][C:15]([C:18]4[N:19]=[N:20][N:21]([CH3:34])[N:22]=4)=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1)[C:3]([O-:5])=[O:4].[CH3:1][CH:2]([CH:6]1[C:10]2=[C:11]([S:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:12]3[C:13]([CH:23]([CH3:24])[CH3:25])=[CH:14][C:15]([C:18]4[N:19]([CH3:34])[N:20]=[N:21][N:22]=4)=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1)[C:3]([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 131726156HCID 131726156, compound

Product 2

HCID 131726154HCID 131726154, compoundHCID 131726155HCID 131726155, compound

Procedure

A solution of the compound of Step 1 in THF (10 mL) was treated with an excess of CH2N2 at 0° C. The reaction mixture was stirred for 5 minutes and the solvent removed. The residue was purified by silica gel chromatography eluted with 50% EtOAc/hexane to give 65 mg of (+/−)-methyl[9-[(4-chlorophenyl)thio]-8-isopropyl-6-(2-methyl-2H-tetrazol-5-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate and 150 mg of (+/−)-methyl[9-[(4-chlorophenyl)thio]-8-isopropyl-6-(1-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate.

Workup

  1. customthe solvent removed
  2. customThe residue was purified by silica gel chromatography
  3. washeluted with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-1690bcb7b8924477a8d87c1f7c2de1e2
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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