Toluene → 4-[(3-Pyridin-3-ylpyrrolidin-1-yl)carbonyl]-3',5'-bis(trifluoromethyl)biphenyl-2-carbohydrazide

HRID 383780Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([C:34]([O:36]C)=O)[C:17]([C:20]4[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=4)=[CH:18][CH:19]=3)=[O:13])[CH2:8]2)[CH:2]=1.O.[NH2:39][NH2:40].C1(C)C=CC=CC=1>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([C:34]([NH:39][NH2:40])=[O:36])[C:17]([C:20]4[CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[C:22]([C:30]([F:33])([F:31])[F:32])[CH:21]=4)=[CH:18][CH:19]=3)=[O:13])[CH2:8]2)[CH:2]=1

Participants

Conditions

Temperature: 135 °C

Procedure

A solution of 7a (160 mg, 0.300 mmol) and hydrazine hydrate (286 μL, 9.18 mmol) in ethanol:toluene (2.70 mL of an 8:1 mixture, respectively) was heated to 100° C. in a sealed microwave vial for 10 min, An additional aliquot of hydrazine hydrate (200 μL, 6.42 mmol) was added, and the resulting mixture was heated to 135° C. in a sealed microwave vial for 15 min. The reaction mixture was cooled to rt and partitioned between EtOAc and water. The combined organics were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 9a. m/z (ES) 523 (MH)+.

Workup

temperatureThe reaction mixture was cooled to rt
custompartitioned between EtOAc and water
washThe combined organics were washed with water and brine
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e60a7281cd324ccdac2978c10961a465
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367679B2

Reaction notes

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