Oxalyl chloride → HCID 11606279, compound

HRID 646867Notes

Reaction equation

HRID 646867 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19][CH2:18]3)[CH:11]=[CH:12][C:13]=2[N+:14]([O-])=O)[CH2:4][CH2:3]1.[C:33]([C:35]1[O:39][C:38]([C:40](O)=[O:41])=[CH:37][CH:36]=1)#[N:34].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>[Pd].CCOC(C)=O.ClCCl>[C:33]([C:35]1[O:39][C:38]([C:40]([NH:14][C:13]2[CH:12]=[CH:11][C:10]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19][CH2:18]3)=[CH:9][C:8]=2[N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[O:41])=[CH:37][CH:36]=1)#[N:34]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 108555165-cyanofuran-2-carboxylic AcidHCID 58638545HCID 58638545, compound

Product 1

HCID 11606279HCID 11606279, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The procedure of Example 4, step (c) was followed using 156 mg (0.348 mmol) of carbonic acid tert-butyl ester 2-{4-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-piperazin-1-yl}-ethyl ester (as prepared in the previous step), 78 mg of 10% palladium on carbon (50% by weight water), 52.5 mg (383 mmol) of 5-cyanofuran-2-carboxylic acid (as prepared in Example 1), 50.1 μL (0.575 mmol) of oxalyl chloride, and 121 μL (0.696 mmol) of DIEA. Chromatography on a 10-g silica SPE column with 5-20% EtOAc-dichloromethane afforded 176 mg (94%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.60 (br s, 1H), 8.29 (d, 1H, J=8.9 Hz), 7.21, 7.24 (AB q, 2H, J=3.7 Hz), 6.79 (d, 1H, J=2.6 Hz), 6.71 (dd, 1H, J=8.9, 2.6 Hz), 4.23 (t, 2H, J=5.8 Hz), 3.16-3.19 (m, 4H), 2.97-3.00 (m, 2H), 2.67-2.75 (m, 8H), 1.82-1.84 (m, 4H), 1.50-1.65 (m, 1H), 1.46-1.58 (m, 2H, partially obscured by t-Bu peak), 1.49 (s, 9H), and 1.07 (d, 3H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C29H39N5O5, 538.3 (M+H) and 438.2 (M-BOC+2H), found 538.2, 438.2.

Sources & evidence

ORD record
ord-4dfef1d1abff40168e824b4e662ba38b
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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