(Z)-tert-butyl 2-chloro-5-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-4H-thieno[3,2-b]pyrrole-4-carboxylate → HCID 178487382, compound

HRID 1844588Notes

Reaction equation

HRID 1844588 reaction equation
[Cl:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]3[CH:11]=[C:12]([O:23][CH3:24])/[C:13](=[CH:15]/[C:16]4[NH:17][C:18]([CH3:22])=[CH:19][C:20]=4[CH3:21])/[N:14]=3)[N:5](C(OC(C)(C)C)=O)[C:4]=2[CH:3]=1>C(O)=O>[Cl:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]3[CH:11]=[C:12]([O:23][CH3:24])/[C:13](=[CH:15]/[C:16]4[NH:17][C:18]([CH3:22])=[CH:19][C:20]=4[CH3:21])/[N:14]=3)[NH:5][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 89500931(Z)-tert-butyl 2-chloro-5-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-4H-thieno[3,2-b]pyrrole-4-carboxylate

Product 1

HCID 178487382HCID 178487382, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of (Z)-tert-butyl 2-chloro-5-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-4H-thieno[3,2-b]pyrrole-4-carboxylate (10 mg) in 2 mL of 88% aqueous formic acid solution was sonicated in an ultrasonic bath for 1 h and then concentrated in vacuo. The residue was purified by Combiflash on a silica gel column eluted with a gradient up to 70% EtOAc/hexanes to give 5 mg of the title compound as a dark solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by Combiflash on a silica gel column
  3. washeluted with a gradient up to 70% EtOAc/hexanes

Sources & evidence

ORD record
ord-dbedc2eeceea48ff865fb05aa99fd130
Source dataset
uspto-grants-2015_02
Patent number
US08946445B2

Reaction notes

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