1,1'-Carbonyldiimidazole → HCID 3159357, compound

HRID 230693Notes

Reaction equation

HRID 230693 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[N:4]=1.[CH:23]([N:26](C(C)C)CC)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.CN>ClCCl>[CH3:23][NH:26][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:12]([N:5]2[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=3[C:3]([C:2]([F:1])([F:22])[F:21])=[N:4]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 8918604-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]benzoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 3159357HCID 3159357, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzoic acid (87 mg, 0.28 mmol) and diisopropylethylamine (0.1 ml) in dichloromethane (3 ml) was treated with 1,1′-carbonyldiimidazole (46 mg, 0.28 mmol) in one portion and stirred at room temperature for 15 minutes. Then methylamine hydrochloride (22 mg, 0.33 mmol) was added and stirring continued for 1 hour. The reaction mix was added to a 5 g pre-packed silica column and eluted with 0-50% ethyl acetate in petroleum ether to give the title compound (28 mg, 31%).

Workup

  1. stirringstirring
  2. waitcontinued for 1 hour
  3. additionThe reaction mix
  4. additionwas added to a 5 g pre-packed silica column
  5. washeluted with 0-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-def1a4c5873f4bdf87bd1e4bbf88d415
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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