Piperidine → HCID 178496943, compound

HRID 577801Notes

Reaction equation

C([N:4]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[N:9]=[CH:8][C:7]=2/[C:6](=[C:17](\OCC)/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[C:5]1=[O:27])(=O)C.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]([CH3:46])[C:36](=[O:45])[CH2:37][N:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]2)=[CH:31][CH:30]=1.N1CCCCC1>CN(C=O)C>[CH3:46][N:35]([C:32]1[CH:31]=[CH:30][C:29]([NH:28]/[C:17](/[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:6]2\[C:5](=[O:27])[NH:4][C:12]3[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[N:9]=[CH:8][C:7]\2=3)=[CH:34][CH:33]=1)[C:36](=[O:45])[CH2:37][N:38]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 110 °C

Procedure

Step-2: To a solution of (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (40 mg, 0.109 mmol) in DMF (0.2 mL) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (28 mg, 0.109 mmol) at room temperature, and the reaction mixture was stirred at 110° C. for 2 h. The reaction mixture was cooled to RT, piperidine (0.2 mL) was added and stirred for 10 minutes at room temperature. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography using 5% CH3OH in dichloromethane as eluent to afford (Z)-methyl 3-(((4-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)phenyl)amino)(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate as yellow solid. MS (ES+): m/z 541.3 (MH+).

Workup

temperatureThe reaction mixture was cooled to RT
stirringstirred for 10 minutes at room temperature
customThe solvent was evaporated
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-b057825dfa5c42cba85dad529fad6974
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040555B2

Reaction notes

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