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

HRID 1820826Notes

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]

Participants

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

washwashed twice with 5 M aq HCl
dry with materialThe organic phase was then dried with Na2SO4
concentrationconcentrated in vacuo
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

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