HCID 136365348, compound → HCID 136189632, compound

HRID 76079Notes

Reaction equation

C([O:5][C:6](=[O:41])[NH:7]/[C:8](=[N:39]\O)/[CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[N:24][C:25]([NH:28][C:29]4[CH:30]=[N:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=4)=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)C(C)C>C1(C)C=CC=C(C)C=1.C1COCC1>[F:36][C:35]([F:37])([F:38])[C:32]1[N:31]=[CH:30][C:29]([NH:28][C:25]2[N:24]=[N:23][C:22]([C:19]3[CH:18]=[CH:17][C:16]([CH:13]4[CH2:12][CH2:11][CH:10]([CH2:9][C:8]5[NH:7][C:6](=[O:41])[O:5][N:39]=5)[CH2:15][CH2:14]4)=[CH:21][CH:20]=3)=[CH:27][CH:26]=2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A solution of [1-[(Z)-hydroxyimino]-2-(4-{4-[6-(6-trifluoromethyl-pyridin-3-ylamino)-pyridazin-3-yl]-phenyl}-cyclohexyl)-ethyl]-carbamic acid isobutyl ester (0.13 g, 0.23 mmol 1.0 equiv) was dissolved in a m-xylene/THF (4:1) mixture and then heated to 180° C. for 20 min. The cooled reaction was partitioned between EtOAc and water, and the organic layers were washed with brine and dried. Purification by silica gel chromatography (10-100% MeOH in DCM) afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.10 (m, 2H) 1.34 (q, J=11.79 Hz, 2H) 1.59 (ddd, J=11.12, 7.58, 4.04 Hz, 1H) 1.70 (t, J=14.02 Hz, 4H) 2.29 (d, J=6.82 Hz, 2H) 2.38-2.46 (m, 1H) 7.23 (d, J=8.08 Hz, 2H) 7.18 (d, J=9.35 Hz, 1H) 7.72 (d, J=8.59 Hz, 1H) 7.84 (d, J=8.08 Hz, 2H) 7.94 (d, J=9.35 Hz, 1H) 8.56 (dd, J=8.59, 1.26 Hz, 1H) 8.81 (d, J=1.77 Hz, 1H) 9.90 (s, 1H) 12.03 (br. S., 1H); (M+H)+497.2.

Workup

customThe cooled reaction
customwas partitioned between EtOAc and water
washthe organic layers were washed with brine
customdried
customPurification by silica gel chromatography (10-100% MeOH in DCM)

Sources & evidence

ORD record: ord-44bfb8199ae94f849985a3f429778e16
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835451B2

Reaction notes

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