Hydrochloric Acid → HCID 86638577, compound

HRID 1807790Notes

Reaction equation

HRID 1807790 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=O)=[CH:4][C:3]=1[F:33].Cl>O1CCCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:32])([C:28]([F:30])([F:31])[F:29])[C:24]([F:25])([F:26])[F:27])=[CH:21][CH:22]=3)[CH2:12][CH2:11]2)=[CH:4][C:3]=1[F:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86638550(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

Product 1

HCID 86638577HCID 86638577, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane tetrahydrofuran complex (13.05 mmol, 1.26 mL, 1.121 g) was added to a solution of (4-amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (1.043 mmol, 0.5 g) in tetrahydrofuran (8 mL) under nitrogen and the reaction heated to reflux for 5.5 hours. 5M Hydrochloric acid (10 mL) was added and the reaction was heated to reflux for 30 minutes, and then was cooled to ambient temperature. The product was extracted into dichloromethane (50 mL), washed with water (3×50 mL), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by preparative HPLC affording the title compound (0.143 g). MS (ESI) m/z 466.0 [M+H]+

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 5.5 hours
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 30 minutes
  5. extractionThe product was extracted into dichloromethane (50 mL)
  6. washwashed with water (3×50 mL)
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-8026d62bc5c64e45ae0f40d661f98936
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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