1,2-Dimethoxyethane → HCID 24751647, compound

HRID 1713116Notes

Reaction equation

[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:25])[CH2:12][N:13]3[CH2:19][CH2:18][C:17]4[C:20](Cl)=[N:21][CH:22]=[N:23][C:16]=4[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(OB([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)O)(=O)C.C([O-])([O-])=O.[Na+].[Na+].C[O:45][CH2:46][CH2:47]OC>O>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:25])[CH2:12][N:13]3[CH2:19][CH2:18][C:17]4[C:20]([C:35]5[CH:34]=[CH:33][C:32]([C:46](=[O:45])[CH3:47])=[CH:37][CH:36]=5)=[N:21][CH:22]=[N:23][C:16]=4[CH2:15][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]-4-chloro-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine (55 mg, 0.15 mmol), acetylphenylboronic acid (37 mg, 0.22 mmol), Pd(PPh)4 (5.5 mg) and Na2CO3 (72 mg) 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 removed in vacuo to give the crude product, which is purified by PTLC (5% MeOH in DCM) to give the title compound. 1H NMR (CDCl3) δ 8.99 (s, 1H), 8.04 (d, 2H), 7.55 (s, 2H), 3.54 (m, 4H), 3.33 (s, 2H), 3.20 (m, 2H), 2.97 (m, 2H), 2.94-2.66 (m, 5H), 2.64 (s, 3H), 2.26 (m, 4H), 2.04 (m, 2H), 1.88 (m, 2H), 1.68 (m, 2H).

Workup

extractionthe mixture is extracted with DCM
dry with materialThe combined organic layers are dried (MgSO4) and solvent
customremoved in vacuo
customto give the crude product, which
customis purified by PTLC (5% MeOH in DCM)

Sources & evidence

ORD record: ord-911d836d2b724655b9274796b3f1eeb6
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795262B2

Reaction notes

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