1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid N'-phenylacetylhydrazide
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.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:44]1([CH2:50][C:51]([NH:53][NH2:54])=[O:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C>[C:44]1([CH2:50][C:51]([NH:53][NH:54][C:11]([C:9]2[NH:8][C:5]3=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[CH:10]=2)=[O:13])=[O:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 8, 50 mg, 0.25 mmol) in DMF (10 mL) was added DIPEA (89 μL, 0.51 mmol), HOBt (34 mg, 0.25 mmol), EDCI (63 mg, 0.33 mmol) and phenylacetic acid hydrazide (38 mg, 0.25 mmol) and the mixture was stirred at rt for 72 h. The reaction mixture was partitioned between water (50 mL) and ethyl acetate (3×30 mL). The combined organics were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude material was chromatographed on silica gel eluting with methanol/dichloromethane (1:19) to give the title compound. m/z (ES+)=329 [M+H]+; RT=3.07 min.
Workup
- customThe reaction mixture was partitioned between water (50 mL) and ethyl acetate (3×30 mL)
- washThe combined organics were washed with brine (20 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe crude material was chromatographed on silica gel eluting with methanol/dichloromethane (1:19)
Sources & evidence
- ORD record
- ord-43d326174526417fbf792cab0f0772fe
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884112B2
Reaction notes
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