S-(N-Boc)-piperidine-3-carboxylhydrazide → HCID 178451956, compound

HRID 646760Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:16]#[N:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][N:7]=1.[NH:18]([C:20]([C@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]1)=O)[NH2:19]>O>[NH2:1][C:2]1[C:3]([C:16]2[NH:19][N:18]=[C:20]([C@@H:22]3[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]3)[N:17]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][N:7]=1

Participants

Conditions

Temperature: 180 °C

Procedure

3-Amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile (514.0 mg, 2.27 mmol) and 1,1-dimethylethyl (3S)-3-(hydrazinocarbonyl)piperidine-1-carboxylate (1.66g, 6.83 mmol) were combined together and heated to 180° C. for 1-2 h. The reaction mixture was poured into water (100 mL), and extracted with ethyl acetate (2×35 mL) then dried over anhydrous sodium sulfate and filteration, concentration and purified by MPLC to give 1,1-dimethylethyl (3R)-3-(5-{3-amino-6-[3-(hydroxymethyl)phenyl]pyrazin-2-yl }-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate. (655.0 mg, 64.2% yield): MS (EI) for C23H29N7O3: 452.29 (MH+).

Workup

extractionextracted with ethyl acetate (2×35 mL)
dry with materialthen dried over anhydrous sodium sulfate and filteration, concentration
custompurified by MPLC

Sources & evidence

ORD record: ord-74d2a71d876748198fc2f5423a79590b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704995B2

Reaction notes

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