Triethylamine → HCID 23114726, compound

HRID 2080460Notes

Reaction equation

O1CCOCC1.Cl.Cl.[Cl:9][C:10]1[C:11]([CH:21]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])=[CH:12][C:13]([NH:16][CH2:17][CH2:18][CH2:19][NH2:20])=[N:14][CH:15]=1.C(N(CC)CC)C.Cl[C:48]1[N:53]=[CH:52][CH:51]=[CH:50][N:49]=1>C(OCC)(=O)C>[Cl:9][C:10]1[C:11]([CH:21]([S:30]([C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)(=[O:31])=[O:32])[C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])=[CH:12][C:13]([NH:16][CH2:17][CH2:18][CH2:19][NH:20][C:48]2[N:53]=[CH:52][CH:51]=[CH:50][N:49]=2)=[N:14][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 1,4-dioxane solution (1.0 ml) of the N-[5-chloro-4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-2-yl]propane-1,3-diamine dihydrochloride (76 mg, 0.136 mmol) obtained in Example 173 were added triethylamine (76 μl, 0.54 mmol) and 2-chloropyrimidine (23 mg, 0.20 mmol). The resulting mixture was stirred at 80° C. for 19 hours. The reaction mixture was allowed to cool to room temperature, followed by dilution with ethyl acetate. The diluted mixture was washed with water and brine, dried and concentrated. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=1:2) to give the title compound (50 mg, 65%). The compound was crystallized in ethanol to afford a white solid (36 mg).

Workup

temperatureto cool to room temperature
washThe diluted mixture was washed with water and brine
customdried
concentrationconcentrated
customThe residue thus obtained
customwas purified by silica gel chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record: ord-b954d4bc60e64489b43bfef022d43ff6
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932271B2

Reaction notes

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