1,1'-Carbonyldiimidazole → imidazol-1-yl-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-methanone

HRID 406459Notes

Reaction equation

[CH:1]1N=[CH:4][N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])[CH:2]=1.[F:13][C:14]([F:26])([F:25])[C:15]1[CH:16]=[N:17][C:18]2CCNC[C:23]=2[CH:24]=1>C1COCC1.C(Cl)Cl>[N:8]1([C:6]([N:3]2[CH2:2][CH2:1][C:18]3[N:17]=[CH:16][C:15]([C:14]([F:26])([F:25])[F:13])=[CH:24][C:23]=3[CH2:4]2)=[O:7])[CH:9]=[CH:10][N:11]=[CH:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of CDI (0.949 g, 5.86 mmol) in THF (10 mL) was added 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,6]naphthyridine (0.988 g, 4.88 mmol) and the reaction mixture was heated at about 60° C. for about 16 h. The reaction mixture was cooled at ambient temperature and concentrated in vacuo to afford a light orange solid. The residue was dissolved in DCM (10 mL), washed with water (2×10 mL), and the organic portion was separated, dried over MgSO4, filtered, and concentrated in vacuo to give imidazol-1-yl-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-methanone (1.28 g, 88%) as a yellow solid which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 2.10 min; m/z: (M+H)+ 297.

Workup

temperatureThe reaction mixture was cooled at ambient temperature
concentrationconcentrated in vacuo
customto afford a light orange solid
washwashed with water (2×10 mL)
customthe organic portion was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1b6b39777c8b429cb7a94ab63a04d143
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754107B2

Reaction notes

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