4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178483560, compound

HRID 2274391Notes

Reaction equation

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

Participants

Conditions

Temperature: 22 °C

Procedure

3.4 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde are added to a solution of 3.5 g of 4-(3-dimethylaminopropoxy)-5-fluorobenzene-1,2-diamine in 150 mL of methanol. The reaction medium is stirred at 22° C. for 18 hours. After evaporation, the reaction crude is purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-330 cartridge. The elution is carried out in dichloromethane with 10% of methanol. 2.3 g of (3-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yloxy}-propyl)dimethylamine are isolated. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.50 to 2.23 (m, 8H); 2.80 (s, 6H); 3.23 (m, 2H); 3.68 (m, 1H); 3.98 (m, 1H); 4.17 (t, J=6.0 Hz, 2H); 5.58 (dd, J=2.5 and 9.5 Hz, 1H); 7.34 (d, J=8.0 Hz, 1H); 7.49 (d, J=11.0 Hz, 1H) 9.11 (s, 1H).

Workup

customAfter evaporation
customthe reaction crude
customis purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-330 cartridge
washThe elution

Sources & evidence

ORD record: ord-ca4c255f7270492caf009ce705aa4cd3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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