Cyclohexene → 2-Amino-N-(5-(3,5-difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)benzamide

HRID 1773382Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[C:35]([F:37])[CH:36]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:33])[C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:19][C:18]=1[N+:30]([O-])=O.C1CCCCC=1>[Pd].O1CCOCC1>[NH2:30][C:18]1[CH:19]=[C:20]([N:23]2[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]2)[CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][C:4]3[CH:34]=[C:35]([F:37])[CH:36]=[C:2]([F:1])[CH:3]=3)[CH:7]=2)[NH:11][N:10]=1)=[O:33]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-[5-(3,5-difluoro-benzyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide (3.21 g, 6.33 mmol), cyclohexene (20 mL), dioxane (200 mL) and 10% Pd/C (0.8 g) was stirred at 100° C. for 2 hours. The reaction mixture was filtered over a celite pad washing thoroughly with THF and MeOH. After evaporation of the organic phase, purification of the crude by chromatography over silica gel (DCM/MeOH 95/5) gave 2.51 g of title compound (83% yield).

Workup

filtrationThe reaction mixture was filtered over a celite pad
washwashing thoroughly with THF and MeOH
customAfter evaporation of the organic phase, purification of the crude by chromatography over silica gel (DCM/MeOH 95/5)

Sources & evidence

ORD record: ord-f8bd02a4d31042979473c3756874ae35
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255087B2

Reaction notes

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