Hydrochloric Acid → HCID 57974150, compound

HRID 1864062Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=2)[NH2:31])[CH2:24][CH2:23]1.Cl>C(O)C>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:7][C:2]([NH:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:28]([N:25]3[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]3)[CH:29]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Ethyl 2-[(2,5-dichloro-4-pyrimidinyl)amino]benzoate (10.2 g, 32.8 mmol) and 3-(4-methyl-1-piperazinyl)aniline (6.6 g, 34.4 mmol) were combined in a vessel with ethanol (200 mL) and concentrated HCl (3.2 mL, 38.4 mmol, 12N). The vessel was sealed and heated with stirring at 95° C. for 24 h. The reaction was cooled to room temperature and poured onto water (1.3 L). The aqueous layer was extracted with ethyl acetate (2×250 mL) and neutralized to pH 7 by the slow addition of 6N NaOH. The precipitated solid was filtered off and washed with water and ethyl ether to afford the product (15.0 g, 98% yield) as a tan solid. MS: M(C24H27ClN6O2)=466.97, (M+H)+=467.2 and 469.2.

Workup

customThe vessel was sealed
temperatureheated
temperatureThe reaction was cooled to room temperature
additionpoured onto water (1.3 L)
extractionThe aqueous layer was extracted with ethyl acetate (2×250 mL)
additionneutralized to pH 7 by the slow addition of 6N NaOH
filtrationThe precipitated solid was filtered off
washwashed with water and ethyl ether

Sources & evidence

ORD record: ord-28599b8a35314a3a98d000107ca49c9a
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625903B2

Reaction notes

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