Potassium Carbonate → HCID 59484931, compound

HRID 2039588Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[N:13]2)=[N:6][CH:7]=1.Cl.Cl[CH2:34][CH2:35][N:36](CCCl)[CH2:37][CH3:38].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[CH3:28][S:25]([C:22]1[CH:21]=[CH:20][C:19]([C:14]2[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][C:10]3[CH:29]=[CH:30][CH:31]=[C:8]([C:5]4[N:4]=[CH:3][C:2]([N:1]5[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]5)=[CH:7][N:6]=4)[CH:9]=3)[N:13]=2)=[CH:24][CH:23]=1)(=[O:27])=[O:26]

Participants

Conditions

Temperature: 130 °C

Procedure

53.3 1.4 g (3.23 mmol) of 2-[3-(5-aminopyrimidin-2-yl)benzyl]-6-(4-methanesulfonylphenyl)-2H-pyridazin-3-one are dissolved in 30 ml of NMP, and 1.59 g (8.72 mmol) of bis(2-chloroethyl)ethylamine hydrochloride and 1.22 g (8.72 mmol) of potassium carbonate are added. The suspension is stirred at 130° C. for 5 days under an argon atmosphere. The reaction mixture is filtered, and the filtrate is stirred into 200 ml of diethyl ether. An oily residue deposits in the process. The residue is purified by means of column chromatography on silica gel. The resultant product is purified by means of preparative HPLC; yield: 41 mg of “A289” trifluoroacetate; HPLC: Rt=2.19 min (method C); LC-MS: 503 (M+H).

Workup

filtrationThe reaction mixture is filtered
stirringthe filtrate is stirred into 200 ml of diethyl ether
customThe residue is purified by means of column chromatography on silica gel
customThe resultant product is purified by means of preparative HPLC

Sources & evidence

ORD record: ord-ca239efe4196411085dfdc82cbd5406e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580781B2

Reaction notes

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