Triethylamine → HCID 58528917, compound

HRID 1431010Notes

Reaction equation

HRID 1431010 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[C:14](F)[C:13]([F:17])=[CH:12][C:11]=2[N+:18]([O-:20])=[O:19])=[N:6][CH:7]=1.[SH:22][C:23]1[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=1.C(N(CC)CC)C>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[C:14]([S:22][C:23]3[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=3)[C:13]([F:17])=[CH:12][C:11]=2[N+:18]([O-:20])=[O:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58528857HCID 58528857, compoundHCID 178480602HCID 178480602, compound

Product 1

HCID 58528917HCID 58528917, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of N-(5-bromo-pyridin-2-yl)-4,5-difluoro-2-nitro-benzamide (236 mg, 0.66 mmol), 2-mercapto-1-methylimidazole (83 mg, 0.73 mmol) and triethylamine (0.18 mL, 1.32 mmol) in 2 mL CH3CN was microwave heated to 130° C. for 10 min and the resulting solid was collected by filtration, rinsed with CH3CN, and dried under high vacuum to provide 214 mg (72%) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 3.70 (s, 3H), 6.91 (d, 1H, J=7 Hz), 7.20 (d, 1H, J=1 Hz), 7.58 (d, 1H, J=1 Hz), 8.07 (br s, 2H), 8.24 (d, 1H, J=10 Hz), 8.47 (br s, 1H), 11.39 (s, 1H); LCMS (m/z): 452/454 [C16H11BrFN5O3S+H]+.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washrinsed with CH3CN
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-125ac07fc72c4867a903888df74d9645
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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