Triethylamine → HCID 66634727, compound

HRID 1911972Notes

Reaction equation

HRID 1911972 reaction equation
ClN1C(=O)CCC1=O.[CH3:9][N:10]([C:17]1[S:18][C:19]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[N:20][N:21]=1)[C:11](=[O:16])[CH2:12][CH2:13][S:14][CH3:15].C(N(CC)CC)C.C(OCC)(=O)C>C1C=CC=CC=1>[CH3:9][N:10]([C:17]1[S:18][C:19]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[N:20][N:21]=1)[C:11](=[O:16])/[CH:12]=[CH:13]/[S:14][CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 66613348HCID 66613348, compound

Product 1

HCID 66634727HCID 66634727, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
23 °C

Procedure

N-Chlorosuccinimide (100 mg, 0.75 mmol, 1.1 equiv) was added to a stirred solution of N-methyl-3-(methylthio)-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)propanamide (200 mg, 0.68 mmol, 1.0 equiv) in benzene (3.3 mL) at 23° C. The resulting cloudy yellow solution was stirred at 23° C. for 30 m. Triethylamine (210 μL, 1.5 mmol, 2.2 equiv) was added and the resulting bright yellow mixture was stirred at 23° C. for 24 h. The reaction mixture was directly subjected to silica gel column chromatography (ethyl acetate) to afford the title compound as a tan powder (80 mg, 40%): 1H NMR (300 MHz, DMSO-d6) δ 9.14 (br s, 1H), 8.67 (m, 1H), 8.27 (m, 1H), 8.11 (d, J=14 Hz, 1H), 7.41 (m, 1H), 6.30 (d, J=14 Hz, 1H), 3.91 (s, 3H), 2.46 (s, 3H); ESIMS m/z 293 ([M+H]+).

Workup

  1. stirringthe resulting bright yellow mixture was stirred at 23° C. for 24 h

Sources & evidence

ORD record
ord-b67abd572b4644d6833636b7fd14d30c
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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