HCID 68312991, compound → HCID 68313053, compound

HRID 1530495Notes

Reaction equation

C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:16]=[C:17]2[C:26](=[CH:27][CH:28]=1)[C:25]1[N:21]([CH:22]=[C:23]([C:29]3[N:33]([CH:34]([CH3:36])[CH3:35])[N:32]=[CH:31][N:30]=3)[N:24]=1)[CH2:20][CH2:19][O:18]2)(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[CH:34]([N:33]1[C:29]([C:23]2[N:24]=[C:25]3[C:26]4[CH:27]=[CH:28][C:15]([C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[S:6]([NH2:5])(=[O:7])=[O:8])=[CH:16][C:17]=4[O:18][CH2:19][CH2:20][N:21]3[CH:22]=2)=[N:30][CH:31]=[N:32]1)([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-tert-butyl-2-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}benzene-1-sulphonamide (200 mg, 0.400 mmol) in TFA (5.0 mL) was heated to 80° C. for 3 h. After concentration, the residue was adjusted to pH around 8, extracted with ethyl acetate (3×50 mL). After removal of the solvent, the residue was purified by reverse phase combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to give 109 (60 mg, 33% yield) as white solid. LCMS (ESI): RT=5.15 min, m/z: 451.2 [M+H+]. 1H NMR (500 MHz, DMSO-d6): δ 8.44-8.41 (m, 1H), 8.07-8.03 (m, 1H), 7.98 (d, J=7.5 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.64-7.56 (m, 3H), 7.39-7.36 (m, 1H), 7.21-7.19 (m, 2H), 7.09 (d, J=5.5 Hz, 1H), 5.97-5.95 (m, 1H), 4.58-4.55 (m, 4H) 1.52-1.49 (m, 6H)

Workup

concentrationAfter concentration
extractionextracted with ethyl acetate (3×50 mL)
customAfter removal of the solvent
customthe residue was purified by reverse phase combiflash
washeluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record: ord-5871c7a2fcf949b5ae7eaab0386f5584
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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