HCID 68033041, compound → HCID 68033046, compound

HRID 522483Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C@@H:13]([NH:20][C:21]([C:23]1[C:27]2[CH2:28][C:29]([CH3:56])([CH3:55])[C:30]3[CH:31]=[N:32][C:33]([NH:36][C:37]4[CH:42]=[CH:41][C:40]([C:43](=[O:52])[NH:44][CH:45]5[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]5)=[CH:39][C:38]=4[O:53][CH3:54])=[N:34][C:35]=3[C:26]=2[O:25][N:24]=1)=[O:22])C1C=CC=CC=1>C1COCC1.NN.O>[NH2:3][C@@H:12]([C:26]1[CH:35]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:13][NH:20][C:21]([C:23]1[C:27]2[CH2:28][C:29]([CH3:55])([CH3:56])[C:30]3[CH:31]=[N:32][C:33]([NH:36][C:37]4[CH:42]=[CH:41][C:40]([C:43](=[O:52])[NH:44][CH:45]5[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]5)=[CH:39][C:38]=4[O:53][CH3:54])=[N:34][C:35]=3[C:26]=2[O:25][N:24]=1)=[O:22]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-[(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-phenylethyl]-8-({2-methoxy-4-[(1-methylpiperidin-4-yl)carbamoyl]phenyl}amino)-5,5-dimethyl-4,5-dihydroisoxazolo[4,5-h]quinazoline-3-carboxamide (60 mg, 0.079 mmol) in THF (3 mL), 35% hydrazine in water (0.07 mL) was added and the reaction was warmed at 70° C. for 24 hours. The reaction was cooled at room temperature diluted with H2O (20 mL) and extracted with DCM (2×20 mL). The organic layers were dried over Na2SO4 and the solvent evaporated to dryness to yield the crude solid that was purified by flash chromatography on silica gel (DCM/MeOH/(NH3 7N in MeOH) to afford the title compounds.

Workup

temperatureThe reaction was cooled at room temperature
extractionextracted with DCM (2×20 mL)
dry with materialThe organic layers were dried over Na2SO4
customthe solvent evaporated to dryness
customto yield the crude solid that
customwas purified by flash chromatography on silica gel (DCM/MeOH/(NH3 7N in MeOH)

Sources & evidence

ORD record: ord-5b16c85e843a4d2682bc050c95bbb398
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09333205B2

Reaction notes

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