Sodium Carbonate → HCID 59463572, compound

HRID 1713150Notes

Reaction equation

[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:24])[CH2:12][N:13]3[CH2:22][CH2:21][C:20]4[CH:19]=[C:18](Cl)[N:17]=[N:16][C:15]=4[CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:24])[CH2:12][N:13]3[CH2:22][CH2:21][C:20]4[CH:19]=[C:18]([C:29]5[CH:30]=[N:25][CH:26]=[N:27][CH:28]=5)[N:17]=[N:16][C:15]=4[CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-3-chloro-5,6,7,8-tetrahydropyrido-[3,4-c]pyridazine (22 mg, 0.06 mmol), 5-pyrimidineboronic acid (12 mg, 0.09 mmol), Pd(PPh)4 (5.5 mg) and Na2CO3 (28 mg, 0.18 mmol) in DME (3 mL) and water (1 mL) is heated overnight at 80° C. Water is added and the mixture is extracted with DCM. The combined organic layers are dried (MgSO4) and solvent is removed in vacuo to give the crude product, which is purified by PTLC (4% TEA in EA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 9.40 (2H, s), 9.36 (1H, s), 7.64 (1H, s), 4.18 (2H, s), 3.84 (4H, m), 3.48 (2H, s), 3.84˜3.16 (4H, m), 2.56-2.64 (1H, m), 2.04-2.20 (4H, m), 1.60-1.98 (6H, m); MS (+VE) m/z 394.2 (M++1).

Workup

extractionthe mixture is extracted with DCM
dry with materialThe combined organic layers are dried (MgSO4) and solvent
customis removed in vacuo
customto give the crude product, which
customis purified by PTLC (4% TEA in EA)

Sources & evidence

ORD record: ord-3cfb0ab661e74dd0b6f7bfe024ad61b6
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795262B2

Reaction notes

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