Hydrochloric Acid → HCID 178487358, compound

HRID 1844583Notes

Reaction equation

HRID 1844583 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[C:6]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[NH:5][C:4]=1[CH:17]=O.[CH3:19][C:20]1[NH:21][CH:22]=[C:23]([CH3:25])[CH:24]=1.Cl>CO.CCOCC>[CH3:25][C:23]1[CH:24]=[C:20]([CH3:19])[NH:21][C:22]=1/[CH:17]=[C:4]1\[N:5]=[C:6]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH:7]=[C:3]\1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 395392,4-DimethylpyrroleHCID 895100773-methoxy-5-(1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 178487358HCID 178487358, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methoxy-5-(1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrrole-2-carbaldehyde (8 mg) and 2,4-dimethyl-1H-pyrrole (3.2 mg) in 1 mL of MeOH was added 2 small drops of a solution of 2 N HCl in ether. The dark-red reaction solution was stirred at r.t. for 1 h and then quenched with 3 mL of pH 7 sodium phosphate buffer solution. The product was extracted with 2×5 mL of EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by Combiflash on a silica gel column eluted with a gradient up to 80% EtOAc/hexanes to give 8 mg of the title compound as a dark solid.

Workup

  1. customquenched with 3 mL of pH 7 sodium phosphate buffer solution
  2. extractionThe product was extracted with 2×5 mL of EtOAc
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by Combiflash on a silica gel column
  7. washeluted with a gradient up to 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-baa1d08d0e7a43009308eb1830add9c2
Source dataset
uspto-grants-2015_02
Patent number
US08946445B2

Reaction notes

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