Potassium Carbonate → HCID 22170965, compound

HRID 2376253Notes

Reaction equation

HRID 2376253 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[Cl:18][C:19]1[CH:20]=[C:21]([C:26](=O)/[CH:27]=[C:28](\O)/[CH2:29][O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH:22]=[CH:23][C:24]=1[Cl:25]>C1COCC1.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:26]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[N:11]=[C:28]([CH2:29][O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[CH:27]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 178520892HCID 178520892, compound

Product 1

HCID 22170965HCID 22170965, compound

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

4-Methoxyphenylhydrazine hydrochloride (3.88 kg, 21.8 mol) and K2CO3 (3.21 kg, 23.2 mol) were added to a THF/EtOAc solution containing (Z)-1-(3,4-dichlorophenyl)-3-hydroxy-4-[(tetrahydro-2H-pyran-2-yl)oxy]-2-buten-1-one (Example 514) at 0-10° C. The resultant suspension was stirred and allowed to warm to rt overnight (16 h). When HPLC analysis indicated the disappearance of the starting material, the reaction mixture was filtered. The organic reaction filtrate was washed with 1 M aq. citric acid (34.0 L), followed by 10% aq. NaCl (50.0 L) and the resulting product solution was used in the next synthetic step without isolation. HPLC (Method U): Rt=16.22 min. MS (ES+): mass calculated for C22H22Cl2N2O3, 432.10; m/z found, 455.1 [M+Na]+. 1H NMR (400 MHz, CDCl3): 7.39 (d, J=1.9 Hz, 1H), 7.33 (d, J=8.5 Hz, 1H), 7.19 (dd, J=6.8, 2.2 Hz, 2H), 6.96 (dd, J=8.1, 2.1 Hz, 1H), 6.87 (dd, J=2.1, 7 Hz, 2H), 6.58 (s, 1H), 4.86 (d, J=12 Hz, 1H), 4.83-4.81(m, 1H), 4.60 (d, J=12 Hz, 1H), 3.99-3.84 (m, 1H), 3.82 (s, 3H), 3.78-3.74 (m, 1H), 1.91-1.52 (m, 6H). 13C NMR (100 MHz, CDCl3): 159.5, 150.7, 141.8, 133.0, 132.7, 130.9, 130.8, 130.6, 128.1, 127.1, 114.7, 107.7, 98.6, 63.2, 62.6, 60.8, 55.9, 30.9, 25.8, 21.4, 19.7, 14.6.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washThe organic reaction filtrate was washed with 1 M aq. citric acid (34.0 L)

Sources & evidence

ORD record
ord-ab4bdb5a6d7f4b60a7badc384fdc0e27
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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