Oxalyl chloride → HCID 11540495, compound

HRID 646863Notes

Reaction equation

HRID 646863 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]([C:32]1[O:36][C:35]([C:37](O)=[O:38])=[CH:34][CH:33]=1)#[N:31].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:37]([C:35]3[O:36][C:32]([C:30]#[N:31])=[CH:33][CH:34]=3)=[O:38])=[C:16]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 108555165-cyanofuran-2-carboxylic AcidHCID 58638536HCID 58638536, compound

Product 1

HCID 11540495HCID 11540495, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure of Example 4, step (c) was followed using 145 mg (0.358 mmol) of 4-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (as prepared in the previous step), 70 mg of 10% palladium on carbon (50% by weight water), 49.1 mg (358 mmol) of 5-cyanofuran-2-carboxylic acid (as prepared in Example 1), 62.4 μL (0.716 mmol) of oxalyl chloride, and 93.6 μL (0.537 mmol) of DIEA. Chromatography on a 20-g silica SPE column with 20-40% EtOAc-dichloromethane followed by recrystallization from EtOAc-hexane afforded 156 mg (88%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.60 (br s, 1H), 8.32 (d, 1H, J=8.9 Hz), 7.22, 7.24 (AB q, 2H, J=3.7 Hz), 6.79 (d, 1H, J=2.6 Hz), 6.72 (dd, 1H, J=8.9, 2.6 Hz), 3.58-3.60 (m, 4H), 3.10 (br s, 4H), 2.97-3.00 (m, 2H), 2.70-2.75 (m, 2H), 1.82-1.85 (m, 2H), 1.55-1.65 (m, 1H), 1.49 (s, 9H), 1.45-1.55 (m, 2H, partially obscured by t-Bu peak) and 1.07 (d, 3H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C28H37N5O4, 494.3 (M+H), found 494.1.

Workup

  1. customChromatography on a 20-g silica SPE column with 20-40% EtOAc-dichloromethane followed by recrystallization from EtOAc-hexane

Sources & evidence

ORD record
ord-ab54674b85fa42589a3661114f778efc
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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