Picolinic acid → HCID 9900588, compound

HRID 1007273Notes

Reaction equation

HRID 1007273 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[NH:8][C:9]([NH:11][NH2:12])=[S:10].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](O)=[O:20].C(N=C=NCCCN(C)C)C>ClCCl>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[NH:8][C:9](=[S:10])[NH:11][NH:12][C:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=1)=[O:20]

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 9900588HCID 9900588, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide (100 mg, 0.545 mmol), picolinic acid (67 mg, 0.545 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (104 mg) in dichloromethane (5 mL) was stirred at room temperature for 24 h and isolated as a white solid (47 mg, 30%). 1H NMR (CDCl3): 10.57 (s, 1H), 9.20 (s, 1H), 8.63 (d, J=4.2 Hz, 1H), 8.06 (d, J=7.5 Hz, 1H), 7.89-7.83 (m, 1H), 7.51-7.47 (m, 1H), 7.02 (brs, 1H), 6.16-6.06 (m, 2H), 4.11 (s, 1H), 2.96 (s, 1H), 2.83 (s, 1H), 1.84-1.76 (m, 1H), 1.38-1.28 (m, 3H).

Sources & evidence

ORD record
ord-29cb29bb90e94f4f98a44f1818a7f79f
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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