Tributylphosphine → 2-(2,4-Dimethoxy-benzyl)-5-(4-methoxyquinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 1591974Notes

Reaction equation

HRID 1591974 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][NH:8][S:7]1(=[O:13])=[O:12].[CH3:20][O:21][C:22]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32]O)=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.C(P(CCCC)CCCC)CCC.CN(C(/N=N/C(N(C)C)=O)=O)C>C1COCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:32][C:28]2[CH:27]=[C:26]3[C:31]([C:22]([O:21][CH3:20])=[CH:23][CH:24]=[N:25]3)=[CH:30][CH:29]=2)[S:7]1(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 5353800DiamideHCID 66751042HCID 66751042, compoundHCID 67138287(4-Methoxyquinolin-7-yl)methanol

Product 1

HCID 671383182-(2,4-Dimethoxy-benzyl)-5-(4-methoxyquinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

745 mg (2.60 mmol) of the title B compound in Example 9, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one, 328 mg (1.73 mmol) of the title E compound, (4-methoxyquinoline-7-yl)-methanol and 448 mg (526 mg., 2.60 mmol) of tributylphosphine are stirred in 5 mL of THF. 448 mg (2.60 mmols) of TMAD is added and the mixture is stirred for 18 h. A spatula tip of Raney nickel is added, the mixture is stirred for 10 min, and then filtered through Celite. The filtrate is evaporated to dryness and chromatographed on a Biotage 40M column with 98:2 EtOAc/EtOH to afford 2-(2,4-dimethoxy-benzyl)-5-(4-methoxy-quinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one: mp=128-132° C.; 1H-NMR (CDCl3) δ 3.79 (2H, s), 3.81 (3H, s), 3.85 (3H, s), 4.06 (3H, s), 4.51 (2H, s), 4.82 (2H, s), 6.46 (2H, m), 6.78 (1H, d, J=5.2) 7.30 (1H, m), 7.53 (1H, dd, J=8.5, 1.5), 7.96 (1H, s), 8.22 (1H, d J=8.5), 8.77 (1H, d, J=5.2); [M+1]+=458.

Workup

  1. stirringthe mixture is stirred for 10 min
  2. filtrationfiltered through Celite
  3. customThe filtrate is evaporated to dryness
  4. customchromatographed on a Biotage 40M column with 98:2 EtOAc/EtOH

Sources & evidence

ORD record
ord-5820bf1e1abf4201a3aad871f15b79c6
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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