1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid N'-(tertbutyloxycarbonyl)hydrazide

HRID 1362936Notes

Reaction equation

HRID 1362936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:5]2=[CH:6][N:7]=1.[C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[NH:15][NH2:16].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.[Cl-].[Na+].O.O>[C:19]([O:18][C:14]([NH:15][NH:16][C:11]([C:9]1[NH:8][C:5]2=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:10]=1)=[O:13])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 598304345-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid N'-(tertbutyloxycarbonyl)hydrazide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 8, 2.05 g, 10.4 mmol) in DMF (30 mL), tert-butyl carbazate (1.38 g, 10.4 mmol), DIPEA (3.5 mL, 20.4 mmol), HOBt (1.58 g, 10.3 mmol) and EDCI (2.54 g, 13.3 mmol) were added successively. The resulting solution was stirred for 12 h at rt before adding water and brine (1:1, 200 mL). The solution was extracted with ethyl acetate (4×50 mL) and the combined organic layers were washed with dilute hydrochloric acid (1N, 50 mL), dilute sodium hydroxide solution (1N, 50 mL) and brine. The organic layer was dried (MgSO4) and concentrated in vacuo to give a solid residue, which was purified by flash chromatography on silica gel (hexane/ethyl acetate, 1:3) to give the title compound. δH (CDCl3): 1.42 (9H, s), 7.19 (1H, s), 7.78 (1H, s), 8.60 (1H, s), 9.28 (1H, br s).

Workup

  1. extractionThe solution was extracted with ethyl acetate (4×50 mL)
  2. washthe combined organic layers were washed with dilute hydrochloric acid (1N, 50 mL), dilute sodium hydroxide solution (1N, 50 mL) and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a solid residue, which
  6. customwas purified by flash chromatography on silica gel (hexane/ethyl acetate, 1:3)

Sources & evidence

ORD record
ord-7c09810c741045f593e2c09c371dba05
Source dataset
uspto-grants-2011_02
Patent number
US07884112B2

Reaction notes

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