Diisopropylethylamine → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid N'-(thiophene-2-yl-aminocarbonyl) hydrazide

HRID 1362930Notes

Reaction equation

CCN(C(C)C)C(C)C.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[N:15]=[C:16]=[O:17].FC(F)(F)C(O)=O.[Cl:25][C:26]1[CH:27]=[C:28]2[CH:34]=[C:33]([C:35]([NH:37][NH2:38])=[O:36])[NH:32][C:29]2=[CH:30][N:31]=1>C1(C)C=CC=CC=1.O1CCOCC1>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[NH:15][C:16]([NH:38][NH:37][C:35]([C:33]1[NH:32][C:29]2=[CH:30][N:31]=[C:26]([Cl:25])[CH:27]=[C:28]2[CH:34]=1)=[O:36])=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

DIPEA (53 μL, 0.31 mmol) and thienyl isocyanate (40 μL, 0.32 mmol) were added to a suspension of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid hydrazide trifluoroacetic acid salt (Preparation 10—route 1, 101 mg, 0.31 mmol) in a mixture of toluene and 1,4-dioxane (10 mL, 1:1). After stirring the mixture at 100° C. for 12 h, the reaction was allowed to cool to rt and the solvent was removed. The remaining oily residue was purified by flash chromatography on silica gel (toluene/acetone:2/1) to give the title compound. δH (CDCl3): 6.60 (1H, d), 6.78 (1H, m), 6.84 (1H, d), 7.26 (1H, d), 7.82 (1H, s), 8.61 (2H, m), 9.97 (1H, s); m/z (ES+)=336 [M+H]+; RT=2.97 min.

Workup

temperatureto cool to rt
customthe solvent was removed
customThe remaining oily residue was purified by flash chromatography on silica gel (toluene/acetone:2/1)

Sources & evidence

ORD record: ord-3e95e8c0814e473486dc2dcdf0e55030
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884112B2

Reaction notes

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