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

Isobutanol → 3-[4-(4-Cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-isobutoxy-benzenesulfonamide

HRID 1820826
Notes
Print preview

Reaction equation

HRID 1820826 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:18]=[C:19]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=3[OH:23])=[O:16])[CH2:11][CH2:10]2)=[CH:5][C:4]=1[F:28])#[N:2].[CH3:29][CH:30]([CH3:33])[CH2:31]O.C1(P(C2C=CC=CC=2)C2C=CC=CN=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:18]=[C:19]([S:24]([NH2:27])(=[O:25])=[O:26])[CH:20]=[CH:21][C:22]=3[O:23][CH2:29][CH:30]([CH3:33])[CH3:31])=[O:16])[CH2:13][CH2:14]2)=[CH:5][C:4]=1[F:28])#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6560IsobutanolHCID 97268Di-tert-butyl azodicarboxylateHCID 6218932-PyridyldiphenylphosphineHCID 690384423-[4-(4-Cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-hydroxy-benzenesulfonamide2×

Product 1

HCID 690383983-[4-(4-Cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-isobutoxy-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 0.1 mmol (3-[4-(4-cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-hydroxy-benzenesulfonamide (compound 6.38), 0.5 mmol 2-methyl-1-propanol and 0.3 mmol diphenyl-2-pyridylphosphine in 4 ml THF was added 0.3 mmol di-tert-butyl azodicarboxylate, and the mixture was stirred at 60° C. for 4 h. The mixture was then diluted with ethyl acetate and washed twice with 5 M aq HCl and then with saturated aq NaCl solution. The organic phase was then dried with Na2SO4, and concentrated in vacuo. The residue was triturated in ether to afford the title compound. MS (m/e): 459.2 ([M−H]−, 100%)

Workup

  1. washwashed twice with 5 M aq HCl
  2. dry with materialThe organic phase was then dried with Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-9a98615c005047058469ce294c529fdf
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07605163B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes