HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → 1-[6-(5-{1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1882007
Notes
Print preview

Reaction equation

HRID 1882007 reaction equation
CC1(C)[O:6][CH:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH:17]([C:25]3[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[C:27]([F:33])[CH:26]=3)[CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:11][CH:12]=2)[CH2:4][O:3]1.C([O-])(=O)C.[NH4+:41].Cl>C(O)(=O)C.C(OCC)(=O)C.O1CCCC1>[F:33][C:27]1[CH:26]=[C:25]([CH:17]([C:16]2[NH:41][C:13]([C:10]3[N:11]=[CH:12][C:7]([CH:5]([OH:6])[CH2:4][OH:3])=[CH:8][CH:9]=3)=[CH:14][CH:15]=2)[CH2:18][CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:30]=[CH:29][C:28]=1[S:31][CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 593314311-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-2-yl]-5-[3-fluoro-4-(methylsulfanyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Product 1

HCID 593313981-[6-(5-{1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 1-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-2-yl]-5-[3-fluoro-4-(methylsulfanyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (500 mg) in acetic acid (5 mL) was added ammonium acetate (1.20 g), and the mixture was stirred at 110° C. for 45 min. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated to give a crude product (400 mg). To a solution of the obtained crude product (400 mg) in tetrahydrofuran (5 mL) was added 1M hydrochloric acid (5 mL), and the mixture was stirred at 50° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (367 mg, quantitatively) as a pale-brown amorphous solid. MS: 457 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a crude product (400 mg)
  7. stirringthe mixture was stirred at 50° C. for 3 hr
  8. washwashed with saturated aqueous sodium hydrogen carbonate
  9. washThe ethyl acetate layer was washed with saturated brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ff45b3000588489688e762875aaa5044
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318746B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes