Hydrochloric Acid → Ethyl 4-({5-fluoro-4-[(2-{[(1 methylethyl)amino]carbonyl}phenyl)amino]-2 pyrimidinyl}amino)benzoate

HRID 1864075Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])[C:5]([F:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1.Cl>C(O)(C)C>[F:21][C:5]1[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[N:7][C:2]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:32][CH:33]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To the solution of 2-[(2-chloro-5-fluoro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide (1.0 g, 3.25 mmol) in isopropanol (30 mL) was added ethyl 4-aminobenzoate (0.59 g, 3.57 mmol, 1.1 eq) followed 0.2 mL of 12N HCl. The reaction mixture was sealed in vessel and heated in a 95° C. oil bath for 16 h. The reaction was cooled to room temperature then white solid was precipitated. The white solid was collected by filtration and washed with cooled isopropyl alcohol (3×5 mL) to give the titled compound (1.1 g, 77% yield). MS: M(C23H23FN5O3)=437.47, (M+H)+=438

Workup

customThe reaction mixture was sealed in vessel
temperatureThe reaction was cooled to room temperature
customwhite solid was precipitated
filtrationThe white solid was collected by filtration
washwashed with cooled isopropyl alcohol (3×5 mL)

Sources & evidence

ORD record: ord-8308d578df2845fd89c57ee0965b6740
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625903B2

Reaction notes

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