Hydrochloric Acid → 2-{[5-(Methoxy)-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}benzamide

HRID 1864050Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.Cl[C:18]1[N:23]=[C:22]([NH:24][C:25]2[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([NH2:29])=[O:28])[C:21]([O:34][CH3:35])=[CH:20][N:19]=1.C(O)(C)C>C1COCC1.C(OCC)C>[CH3:35][O:34][C:21]1[C:22]([NH:24][C:25]2[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([NH2:29])=[O:28])=[N:23][C:18]([NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[C:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:10]=2)=[N:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-[2-(4-Morpholinyl)ethyl]aniline (103 mg; 0.5 mmoles) was dissolved in THF (2 mL) and treated with 1 mL of a solution of 1M HCl in ethyl ether. The mixture was stirred for 5 min and then concentrated in vacuo. The residue was treated with 2-{[2-chloro-5-(methoxy)-4-pyrimidinyl]amino}benzamide (139 mg; 0.5 mmoles) and isopropanol (4 mL). The suspension was stirred in a vial, which was sealed and heated at 100° C. for 24 h. Upon cooling, the solid was collected by filtration, washed with cold isopropanol and dried in vacuo to afford the desired product. MS: (M+H)+=449.

Workup

concentrationconcentrated in vacuo
stirringThe suspension was stirred in a vial, which
customwas sealed
temperatureUpon cooling
filtrationthe solid was collected by filtration
washwashed with cold isopropanol
customdried in vacuo

Sources & evidence

ORD record: ord-65cb3c03911a4d0b985975e7f1a7ef22
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625903B2

Reaction notes

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