4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178526766, compound

HRID 2274410Notes

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].[F:17][C:18]1[CH:19]=[C:20]([NH2:32])[C:21]([NH2:31])=[CH:22][C:23]=1[N:24]1[CH2:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C=O)C>[F:17][C:18]1[C:23]([N:24]2[CH2:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:22][C:21]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:32][C:20]=2[CH:19]=1

Participants

Conditions

Temperature: 22 °C

Procedure

3 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde and 43 mg of ferric chloride are added to a solution of 3 g of 4-fluoro-5-perhydro-1,4-oxazepin-4-ylbenzene-1,2-diamine in 60 mL of DMF. The reaction medium is stirred at 22° C. for 16 hours. After evaporation, the reaction crude is purified by flash chromatography. The elution is carried out in a 1/1 mixture of cyclohexane/ethyl acetate. 3 g of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-perhydro-1,4-oxazepin-4-yl-1H-benzimidazoleare isolated in the form of a red oil. 1H NMR (400 MHz, DMSO-d6, δ in ppm): from 1.40 to 2.25 (m, 8H); from 3.25 to 3.39 (m partially masked, 4H); 3.70 (m, 1H); 3.78 (m, 4H); 3.99 (m, 1H); 5.59 (dd, J=2.5 and 9.5 Hz, 1H); 7.16 (broad m, 1H); 7.39 (broad d, J=11.5 Hz, 1H); 9.17 (s, 1H); 12.75 (broad m, 1H).

Workup

customAfter evaporation
customthe reaction crude
customis purified by flash chromatography
washThe elution
additionis carried out in a 1/1 mixture of cyclohexane/ethyl acetate
custom3 g of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-perhydro-1,4-oxazepin-4-yl-1H-benzimidazoleare isolated in the form of a red oil

Sources & evidence

ORD record: ord-aefce693d0c1493eb0ed312785c86f65
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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