Pyrrolidine → HCID 4862343, compound

HRID 230650Notes

Reaction equation

HRID 230650 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.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>ClCCl>[N:35]1([C:16]([C:15]2[CH:19]=[CH:20][C:12]([N:5]3[C:6]4[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=4[C:3]([C:2]([F:21])([F:22])[F:1])=[N:4]3)=[CH:13][CH:14]=2)=[O:18])[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 8918604-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]benzoic acid

Product 1

HCID 4862343HCID 4862343, compoundYield 50.1%

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) in dichloromethane (3 ml) was treated in one portion with solid 1,1′-carbonyldiimidazole (46 mg, 0.28 mmol). This mixture was allowed to stir at room temperature for 15 minutes. Pyrrolidine (23 mg, 0.32 mmol) was then added and the stirring continued for 1 hour at room temperature. The reaction mixture was then added to a 5 g pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a yellow oil (51 mg, 50%).

Workup

  1. waitthe stirring continued for 1 hour at room temperature
  2. additionThe reaction mixture was then added to a 5 g pre-packed silica column
  3. washeluted from 0-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-ac919f1f9cbc4999826bfab85498816d
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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