Acetic Acid → HCID 178433040, compound

HRID 1695808Notes

Reaction equation

C([O:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[N:15][NH:16]3)=[C:12]([NH:19][C:20]([C:22]3[N:23]=[C:24]([CH3:27])[S:25][CH:26]=3)=[O:21])[CH:11]=2)=[CH:6][C:5]=1[NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])C.C(O)(=O)C.Cl>O>[OH:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[N:15][NH:16]3)=[C:12]([NH:19][C:20]([C:22]3[N:23]=[C:24]([CH3:27])[S:25][CH:26]=3)=[O:21])[CH:11]=2)=[CH:6][C:5]=1[NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:30])=[O:31]

Participants

Conditions

Temperature: 100 °C

Procedure

N-(6-{6-(Ethyloxy)-5-[(phenylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (24 mg) was weighed to a microwave vial and acetic acid (0.25 ml) and concentrated HCl (0.25 ml) were added. The reaction was heated under microwave irradiation for 10 min at 100° C. The reaction was cooled to RT and then heated again under microwave irradiation for 10 min at 100° C. Water was added to the reaction and the resultant precipitate was collected by filtration. The precipitate was dissolved into MeOH:DCM then evaporated to dryness. The residue was then dissolved in DMSO:MeOH (0.8 ml, 1:1, v/v) and purified by MDAP (method F) to give the title compound (6.5 mg).

Workup

additionwere added
temperatureThe reaction was cooled to RT
temperatureheated again under microwave irradiation for 10 min at 100° C
filtrationthe resultant precipitate was collected by filtration
dissolutionThe precipitate was dissolved into MeOH
customDCM then evaporated to dryness
dissolutionThe residue was then dissolved in DMSO
customMeOH (0.8 ml, 1:1, v/v) and purified by MDAP (method F)

Sources & evidence

ORD record: ord-de3e6d9a0c994c1c842dcf6619131e56
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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