Triethylamine → HCID 13478095, compound

HRID 280095Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

2.25 g 2-Chloroquinazoline, 4.2 g 1-(3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl)piperazine and 2 ml triethylamine in 8 ml isopropanol are stirred and heated 21/2 hours at 80° C. The solvent is then evaporated in vacuo and the residue is taken up in hexane. The hexane solution is treated with charcoal, filtered and concentrated whereby the ketal of the title compound crystallizes out. The resulting precipitate is dissolved in 40 ml aqueous 1N hydrochloric acid. After 1 hour the acidic solution is made alkaline with aqueous ammonia. The resulting precipitate is filtered off and recrystallized from ethyl acetate to give the title compound, m.p. 129°-131° C.

Workup

customThe solvent is then evaporated in vacuo
additionThe hexane solution is treated with charcoal
filtrationfiltered
concentrationconcentrated whereby the ketal of the title compound
customcrystallizes out
dissolutionThe resulting precipitate is dissolved in 40 ml aqueous 1N hydrochloric acid
filtrationThe resulting precipitate is filtered off
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-08454f3608f04742afd7aee3d64b3985
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04588725

Reaction notes

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