Potassium Carbonate → HCID 59484931, compound

HRID 1408405Notes

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-8b2b8b6670d94fd0b8a98ec086b37934
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921357B2

Reaction notes

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