Triethylamine → HCID 22480319, compound

HRID 1349593Notes

Reaction equation

HRID 1349593 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl.[CH3:28][O:29][C:30](=[O:40])[C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:35]([C:34]3[CH:38]=[CH:39][C:31]([C:30]([O:29][CH3:28])=[O:40])=[CH:32][CH:33]=3)=[O:36])=[CH:10][CH:11]=2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22480178HCID 22480178, compoundHCID 66646188HCID 66646188, compound

Product 1

HCID 22480319HCID 22480319, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a flask containing 1-acetyl-5-amino-3-phenyl-1H-indazole (300 mg, 1.2 mmol) was added dichloromethane (10 mL), 4-(dimethylamino)pyridine (75 mg, 0.6 mmol) and triethylamine (180 mg, 1.8 mmol). The mixture was allowed to stir for ten minutes. Terephthalic acid monomethyl ester hydrochloride (285 mg, 1.44 mmol) was then added and stirring continued for 18 hours. The mixture was quenched with 5% sodium bicarbonate and extracted with dichloromethane. The extracts were dried using sodium sulfate, filtered and condensed to give a solid. The solid was recrystallized in ethanol to give the title compound (368 mg, 75% yield). ES-MS (m/z) 414 [M+1]+.

Workup

  1. stirringstirring
  2. customThe mixture was quenched with 5% sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. customThe extracts were dried
  5. filtrationfiltered
  6. customcondensed
  7. customto give a solid
  8. customThe solid was recrystallized in ethanol

Sources & evidence

ORD record
ord-d2ca719d6dc64c95a9f94c6582f8f125
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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