Phthalic Anhydride → 2-({3-[2-(4-Fluorophenyl)-3-(methylcarbamoyl)-2H-indazol-6-yl]phenyl}carbamoyl)benzoic acid

HRID 1037565Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:12]=3[C:24]([NH:26][CH3:27])=[O:25])[CH:5]=[CH:6][CH:7]=1.[C:28]1(=[O:38])[O:33][C:31](=[O:32])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12>C(#N)C>[F:23][C:20]1[CH:21]=[CH:22][C:17]([N:13]2[C:12]([C:24](=[O:25])[NH:26][CH3:27])=[C:11]3[C:15]([CH:16]=[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:28]([C:29]5[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=5[C:31]([OH:33])=[O:32])=[O:38])[CH:7]=[CH:6][CH:5]=4)[CH:9]=[CH:10]3)=[N:14]2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of Compound (16) (10 mg, 0.03 mmol) in ACN (3 mL) was added phthalic anhydride (8.2 mg, 0.06 mmol) and the reaction mixture was heated to 70° C. and stirred for 15 h. The reaction mixture was then cooled to RT and the resulting precipitate was collected by filtration. The residue was washed with cold ACN (5 mL) to afford Compound (17) as an off-white amorphous solid (7.83 mg, 55%). ESI-MS m/z calculated for [M+H]+: 509.15; found: 509.08. 1H NMR (400 MHz, d6-DMSO) δ 13.07 (brs, 1H), 10.47 (s, 1H), 8.77-8.71 (m, 1H), 7.99-7.87 (m, 3H), 7.77-7.38 (m, 12H), 2.85 (d, J=4.5 Hz, 3H).

Workup

temperatureThe reaction mixture was then cooled to RT
filtrationthe resulting precipitate was collected by filtration
washThe residue was washed with cold ACN (5 mL)

Sources & evidence

ORD record: ord-22fcd8d8baab48c899bd0180090912b8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546389B2

Reaction notes

Loading…