Triethylamine → {1-[4-(4-Fluoro-phenyl)phthalazin-1-yl]piperidin-4-yl}-methyl-carbamic acid tert-butyl ester

HRID 1012960

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

Add 1-chloro-4-(4-fluorophenyl)-phthalazine (3.00 g, 11.6 mmol) to a solution of methyl-piperidin-4-yl-carbamic acid tert-butyl ester (2.98 g, 13.9 mmol) and triethylamine (3.52 g., 34.8 mmol) in DMF (30 mL). Heat at 130° C. for 3 days. Dissolve the reaction mixture in dichloromethane and wash with brine. Dry the organic phase with sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography (20:5:1, hexane:ethyl acetate: 2 M ammonia in methanol) to yield the title compound as a solid (4.45 g, 88%). ES/MS m/z 437.2 (M+1).

Workup

washwash with brine
dry with materialDry the organic phase with sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customPurify the resulting residue by flash chromatography (20:5:1, hexane:ethyl acetate: 2 M ammonia in methanol)

Sources & evidence

ORD record: ord-5c9f3cc8906441889ca44d7048524c4d
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981892B2

Linked notes

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