1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,4-Dichlorobenzoic acid N'-(5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carbonyl)hydrazide

HRID 1362935Notes

Reaction equation

HRID 1362935 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([OH:13])=O)[NH:10][C:5]2=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:18]([NH:20][NH2:21])=[O:19].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([NH:21][NH:20][C:18](=[O:19])[C:17]3[CH:22]=[CH:23][C:24]([Cl:25])=[C:15]([Cl:14])[CH:16]=3)=[O:13])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3119963,4-DichlorobenzhydrazideHCID 116655855-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

Product 1

HCID 598304143,4-Dichlorobenzoic acid N'-(5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carbonyl)hydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (Preparation 5, 20.0 mg, 0.10 mmol) in DMF (5 mL) was added 3,4-dichlorobenzoic acid hydrazide (23 mg, 0.11 mmol), DIPEA (19.5 μL, 0.11 mmol) and HOBt (14.0 mg, 0.10 mmol). The resulting solution was stirred for 5 min prior to the addition of EDCI (23 mg, 1.20 mmol). The reaction mixture was stirred for 16 hr at rt then partitioned between water (10 mL) and dichloromethane (20 mL) on a hydrophobic frit. The aqueous phase was extracted with a further portion of dichloromethane (30 mL) and the combined organics were concentrated in vacuo. Trituration of the resulting residue with ethyl acetate/dichloromethane gave the title compound. δH (d6 DMSO): 12.25 (1H, s), 10.83 (2H, d), 8.17 (1H, s), 7.55-7.97 (3H, m), 7.38 (1H, s), 7.26 (1H, d); m/z (ES+)=383 [M+H]+; RT=3.37 min.

Workup

  1. stirringThe reaction mixture was stirred for 16 hr at rt
  2. customthen partitioned between water (10 mL) and dichloromethane (20 mL) on a hydrophobic frit
  3. extractionThe aqueous phase was extracted with a further portion of dichloromethane (30 mL)
  4. concentrationthe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-64b229b7923f455bbdbe4bf51c715732
Source dataset
uspto-grants-2011_02
Patent number
US07884112B2

Reaction notes

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