1,3-Benzodioxole-5-carboxylic acid → HCID 59830417, compound

HRID 1362932Notes

Reaction equation

HRID 1362932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][NH2:14])=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[C:45](O)(=[O:55])[C:46]1[CH:54]=[CH:53][C:52]2[O:51][CH2:50][O:49][C:48]=2[CH:47]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][NH:14][C:45]([C:46]3[CH:54]=[CH:53][C:52]4[O:51][CH2:50][O:49][C:48]=4[CH:47]=3)=[O:55])=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1

Participants

8

Reactant 5

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 598304225-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid hydrazide

Product 1

HCID 59830417HCID 59830417, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid hydrazide (Preparation 10—route 2, 0.100 g, 0.48 mmol) in DMF (4 mL) was added HOBt (0.064 g, 0.48 mmol), EDCI (0.110 g, 0.58 mmol), DIPEA (200 μL, 0.96 mmol) and piperonylic acid (0.079 g, 0.48 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was poured into water (75 mL) and extracted with ethyl acetate (2×150 mL). The combined organic extract was washed with saturated sodium chloride (75 mL), dried (MgSO4) and concentrated in vacuo to give a solid. The solid obtained was purified by recrystallisation from methanol to give the title compound. m/z (ES+)=359 [M+H]+; RT=2.92 min.

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. extractionThe combined organic extract
  3. washwas washed with saturated sodium chloride (75 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customThe solid obtained
  8. customwas purified by recrystallisation from methanol

Sources & evidence

ORD record
ord-f051d914643d464fb4d719d459964c3e
Source dataset
uspto-grants-2011_02
Patent number
US07884112B2

Reaction notes

Loading…