4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178452212, compound

HRID 2274434Notes

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].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[C:34]([NH2:36])[C:33]([NH2:37])=[CH:32][C:31]=2[F:38])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CO>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([C:30]2[C:31]([F:38])=[CH:32][C:33]3[N:37]=[C:15]([C:5]4[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][N:7]([CH:9]5[CH2:14][CH2:13][CH2:12][CH2:11][O:10]5)[N:6]=4)[NH:36][C:34]=3[CH:35]=2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 22 °C

Procedure

0.9 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde is added to a solution of 1.2 g of 4-(4,5-diamino-2-fluorophenyl)piperazine-1-carboxylic acid tert-butyl ester in 30 mL of methanol. The reaction medium is stirred at 22° C. for 16 hours. After evaporation, the reaction crude is purified by flash chromatography, elution being carried out with a mixture of dichloromethane/acetone. 530 mg of 4-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yl}piperazine-1-carboxylic acid tert-butyl ester are isolated in the form of a red foam. 1H NMR (400 MHz, DMSO-d6, δ in ppm): from 1.35 to 2.25 (m, 6H); 1.43 (s, 9H); 3.03 (m, 4H); 3.52 (m, 4H); 3.72 (m, 1H); 4.00 (m, 1H); 5.65 (dd, J=2.0 and 10.0 Hz, 1H); 7.31 (d, J=8.0 Hz, 1H); 7.54 (d, J=12.0 Hz, 1H); 9.17 (s, 1H). ES mass spectrum: m/z=516 MH+ (base peak).

Workup

customAfter evaporation
customthe reaction crude
customis purified by flash chromatography, elution
additionbeing carried out with a mixture of dichloromethane/acetone

Sources & evidence

ORD record: ord-e5d76747358d4d04950176e1980e5887
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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