Pyrrolidine → HCID 57762788, compound

HRID 230648Notes

Reaction equation

HRID 230648 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[F:18][C:19]([F:39])([F:38])[C:20]1[C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[N:22]([C:29]2[CH:37]=[CH:36][C:32](C(O)=O)=[CH:31][CH:30]=2)[N:21]=1.C([N:43]([CH:46](C)C)CC)(C)C.[NH:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1>O1CCOCC1>[F:38][C:19]([F:39])([F:18])[C:20]1[C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[N:22]([C:29]2[CH:30]=[CH:31][C:32]([NH:43][C:46]([N:49]3[CH2:53][CH2:52][CH2:51][CH2:50]3)=[O:8])=[CH:36][CH:37]=2)[N:21]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 8918604-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]benzoic acid

Product 1

HCID 57762788HCID 57762788, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diphenylphosphoryl azide (290 μL; 1.36 mmol) was added in one portion to a stirring mixture of 4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzoic acid (195 mg; 0.63 mmol) and diisopropylethylamine (220 μL; 1.29 mmol) in 1,4-dioxane (2.2 mL). The mixture was heated at reflux for 2 hours, pyrrolidine (100 μL; 1.21 mmol) was added in on portion, and the reaction heated at reflux for a further 1 hour. Concentration in vacuo, followed by column chromatography gave the title compound (38 mg; 16%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturethe reaction heated
  4. temperatureat reflux for a further 1 hour
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-09e29bfbdcd2455db257717e4d626258
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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