Potassium Carbonate → HCID 59484931, compound

HRID 925488Notes

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-3411acf68da44eb2a333486f955d71ba
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284300B2

Reaction notes

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