Hydrochloric Acid → 1-(3-(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(pyridin-4-yl)urea

HRID 1807794Notes

Reaction equation

HRID 1807794 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl.[CH3:36][CH:37](O)[CH3:38]>ClCCl.[K].[Fe]>[F:1][C:2]([F:34])([F:33])[C:3]([C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]([C:22]3[CH:23]=[C:24]([NH:28][C:20]([NH:17][C:37]4[CH:38]=[CH:15][N:14]=[CH:13][CH:36]=4)=[O:21])[CH:25]=[CH:26][CH:27]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 86638578(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)(3-nitrophenyl)methanone

Product 1

HCID 591759031-(3-(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(pyridin-4-yl)urea

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 6344DichloromethaneSolventHCID 5462222PotassiumSolvent

Procedure

To a stirred suspension of (4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)(3-nitrophenyl)methanone (1.730 mmol, 850 mg) and iron powder (17.30 mmol, 966 mg) in 2-propanol was added a small volume of hydrochloric acid (37%). The reaction was refluxed for 1 hour then was allowed to cool to room temperature. The reaction was diluted with dichloromethane and solid potassium carbonated was added. The reaction was stirred for 1 hour then was filtered through celite washing with dichloromethane. The filtrate was concentrated under reduced pressure. The crude material was chromatographed on silica eluting with ethyl acetate to give the title compound (440 mg). MS (ESI) m/z 462.2 [M+H]+

Workup

  1. temperatureThe reaction was refluxed for 1 hour
  2. additionwas added
  3. filtrationthen was filtered
  4. washthrough celite washing with dichloromethane
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe crude material was chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-40812a623e1f43b4b68a33fc6127b29c
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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