HCID 67050723, compound → HCID 67050837, compound

HRID 1498472Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][C:7]([C:10]2[CH:31]=[CH:30][C:13]3[C:14]4[N:18]([CH2:19][CH2:20][O:21][C:12]=3[CH:11]=2)[CH:17]=[C:16]([C:22]2[N:23]([CH:27]([CH3:29])[CH3:28])[N:24]=[CH:25][N:26]=2)[N:15]=4)=[C:6]([C:32]([NH2:34])=[O:33])[CH2:5]1)([CH3:3])[CH3:2]>[Pt](=O)=O>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:31]=[CH:30][C:13]3[C:14]4[N:18]([CH:17]=[C:16]([C:22]5[N:23]([CH:27]([CH3:29])[CH3:28])[N:24]=[CH:25][N:26]=5)[N:15]=4)[CH2:19][CH2:20][O:21][C:12]=3[CH:11]=2)[CH:6]([C:32]([NH2:34])=[O:33])[CH2:5]1)([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-isopropyl-4-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid amide (153 mg, 0.33 mmol) in IMS (denatured ethanol) (10 mL) was added platinum (IV) oxide (15 mg, 0.06 mmol). The reaction mixture was heated at 50° C. under an atmosphere of hydrogen. The reaction mixture was cooled to RT, filtered through Celite® and the filtrate concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 10 to 20% methanol in DCM) to give 403 (80 mg, 52%). LCMS: RT=2.61 min, [M+H]+=464. 1H NMR 400 MHz (DMSO-d6) δ: 8.38 (1 H, d, J=8.33 Hz), 8.15 (1 H, s), 8.04 (1 H, s), 7.04 (1 H, dd, J=8.35, 1.82 Hz), 6.89 (1 H, d, J=1.72 Hz), 5.86 (1 H, m), 4.57-4.48 (4 H, m), 3.57 (2 H, t, J=12.74 Hz), 3.42 (1 H, m), 3.31 (1 H, m), 3.25 (1 H, m), 3.22 (1 H, m), 3.04 (1 H, s), 2.60 (1 H, d, J=13.63 Hz), 1.96 (1 H, s), 1.50 (6 H, dd, J=6.59, 3.63 Hz), 1.30 (3 H, d, J=6.70 Hz), 1.22 (3 H, d, J=6.70 Hz)

Workup

temperatureThe reaction mixture was cooled to RT
filtrationfiltered through Celite®
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-4d490973eb4044369a42e53ab13fae9e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198918B2

Reaction notes

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