Triethylamine → 1-{4-[2-(3,3-difluoro-1-pyrrolidinyl)-2-oxoethyl]phenyl}-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

HRID 230672Notes

Reaction equation

HRID 230672 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19](O)=[O:20])=[CH:14][CH:13]=2)[N:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[F:37][C:38]1([F:43])[CH2:42][CH2:41][NH:40][CH2:39]1.C(N(CC)CC)C>ClCCl>[F:37][C:38]1([F:43])[CH2:42][CH2:41][N:40]([C:19](=[O:20])[CH2:18][C:15]2[CH:14]=[CH:13][C:12]([N:5]3[C:6]4[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=4[C:3]([C:2]([F:22])([F:1])[F:23])=[N:4]3)=[CH:17][CH:16]=2)[CH2:39]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 50992931{4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetic acid

Product 1

HCID 248258051-{4-[2-(3,3-difluoro-1-pyrrolidinyl)-2-oxoethyl]phenyl}-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazoleYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetic acid (65 mg, 0.2 mmol) in dichloromethane (2 ml) was treated in one portion with solid 1,1′-carbonyldiimidazole (33 mg, 0.2 mmol). This mixture was allowed to stir at room temperature for 15 minutes. 3,3-difluoropyrrolidine hydrochloride (29 mg, 0.2 mmol) was then added followed by triethylamine (21 mg, 0.21 mmol) and the stirring continued for 1 hour at room temperature. The reaction mixture was reduced to minimum volume under reduced pressure then purified by mass directed auto-prep to give the title compound as a yellow oil (53 mg, 64%).

Workup

  1. waitthe stirring continued for 1 hour at room temperature
  2. customthen purified by mass

Sources & evidence

ORD record
ord-abae3ea564494b6cadd0acd3678af797
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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