Triethylamine → HCID 135427920, compound

HRID 1924433Notes

Reaction equation

FC(F)(F)S(OC)(=O)=O.[OH:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([NH:17][CH3:18])=O)=[CH:13][CH:12]=1.C(N(CC)CC)C.[CH3:28][N:29]1[C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:38]([NH:40][NH2:41])=O)[C:32]=2[CH:31]=[CH:30]1>C1(C)C=CC=CC=1.CN(C=O)C>[CH3:18][N:17]1[C:38]([C:33]2[CH:34]=[CH:35][CH:36]=[C:37]3[C:32]=2[CH:31]=[CH:30][N:29]3[CH3:28])=[N:40][N:41]=[C:15]1[C:14]1[CH:19]=[CH:20][C:11]([OH:10])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Methyl trifluoromethanesulfonate (200 μL, 1.76 mmol) was added to 4-hydroxy-N-methylbenzamide (6-A) (133 mg, 0.881 mmol) and the mixture stirred at 65° C. for 10 min. Toluene (0.6 mL) was added and the suspension stirred rapidly at 65° C. for 30 min. Toluene (0.4 mL), triethylamine (370 μL, 2.67 mmol) and a solution of 1-methyl-1H-indole-4-carbohydrazide (6-B) (100 mg, 0.528 mmol) in toluene (1.0 mL) and DMF (250 μL) were added and the mixture stirred at 65° C. for 3 h and then at 125° C. for 18 h. The mixture was evaporated in vacuo and the residue purified by preparative TLC (silica gel, methylene chloride:methanol, 95:5) to provide 4-[4-methyl-5-(1-methyl-1H-indol-4-yl)-4H-1,2,4-triazol-3-yl]phenol (6-C). 1H NMR (500 MHz, CD3OD): δ 3.63 (s, 3H); 3.92 (s, 3H); 6.53 (d, 1H); 7.00 (d, 2H); 7.37 (m, 3H); 7.64, (m, 3H).

Workup

stirringthe suspension stirred rapidly at 65° C. for 30 min
stirringthe mixture stirred at 65° C. for 3 h
waitat 125° C. for 18 h
customThe mixture was evaporated in vacuo
customthe residue purified by preparative TLC (silica gel, methylene chloride:methanol, 95:5)

Sources & evidence

ORD record: ord-ffe11bd0661a4b3daff51184ff03ab45
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178546B2

Reaction notes

Loading…