Dimethylformamide → HCID 10304111, compound

HRID 1250227Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]2[N:17]([CH2:18][CH2:19][CH2:20]I)[C:16](=[O:22])[C:15]3[C:10](=[C:11]([O:23][CH3:24])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:33][N:34]([CH:36]=O)[CH3:35]>CCOC(C)=O>[ClH:1].[ClH:1].[N:34]1([CH:35]2[CH2:11][CH2:10][N:9]([CH2:20][CH2:19][CH2:18][N:17]3[C:16](=[O:22])[C:15]4[C:10](=[C:11]([O:23][CH3:24])[CH:12]=[CH:13][CH:14]=4)[N:9]=[C:8]3[CH2:7][O:6][C:5]3[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:8][CH2:7]2)[CH2:36][CH2:26][CH2:2][CH2:3][CH2:33]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of the product from Step B (90 mg, 0.186 mmol), 4-piperidine-piperidine (125 mg, 0.743 mmol) and K2CO3 (102 mg, 0.743 mmol) in DMF (5 mL) was heated at 70° C. for 17 h. The reaction mixture was diluted with EtOAc and the organic solution was washed with H2O, dried and concentrated. The crude residue was purified by SiO2-gel chromatography (10% NEt3/EtOAc). This product was dissolved in 4.0 M HCl in 1,4-dioxane (1 mL) and concentrated to give the desired compound (72 mg, 74%). API-MS: 526 (M+1). 1H NMR (300 MHz, d4-MeOH): d 7.8 (d, 1 H), 7.5 (t, 1 H), 7.45 (d, 1 H), 7.3 (d, 2 H), 7.15 (d, 2 H), 5.35 (s, 2 H), 4.3 (t,2 H), 4.0 (s, 3 H), 3.8 (d, 1 H), 3.45 (d, 1 H), 3.1 (m, 2 H), 2.5-1.8 (m).

Workup

washthe organic solution was washed with H2O
customdried
concentrationconcentrated
customThe crude residue was purified by SiO2-gel chromatography (10% NEt3/EtOAc)
dissolutionThis product was dissolved in 4.0 M HCl in 1,4-dioxane (1 mL)
concentrationconcentrated

Sources & evidence

ORD record: ord-9d287998ba7d4be6ae29eb019ecad177
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337332B1

Reaction notes

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