Diisopropylethylamine → 1-(2-(4-(Benzo[d]thiazol-2-ylsulfonyl)-3-oxopiperazin-1-yl)-2-oxoethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

HRID 857563Notes

Reaction equation

HRID 857563 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[O:26])(=[O:19])=[O:18].[N:27]1([CH2:36][C:37](O)=[O:38])[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]1=[O:29].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17]([N:20]1[CH2:25][CH2:24][N:23]([C:37](=[O:38])[CH2:36][N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:22][C:21]1=[O:26])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 2724699PyBOPHCID 685235511-(Benzothiazole-2-sulfonyl)-piperazin-2-one trifluoroacetic acid salt

Product 1

HCID 112712061-(2-(4-(Benzo[d]thiazol-2-ylsulfonyl)-3-oxopiperazin-1-yl)-2-oxoethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 1-(benzothiazole-2-sulfonyl)-piperazin-2-one trifluoroacetic acid salt (0.83 g, 2.5 mmol), (thymin-1-yl)-acetic acid (0.46 g, 2.5 mmol), and PyBOP (1.43 g, 2.75 mmol) in DMF (12 mL) was added diisopropylethylamine (0.61 ml, 3.75 mmol) at ambient temperature. The resulting reaction mixture was stirred for 4 h at the same temperature and the solvent was removed in vacuo. The residue was dissolved in dichloromethane (20 mL) and the solution was washed with water, saturated sodium bicarbonate solution, 1N HCl solution, and saline. The resulting solution was dried over magnesium sulfate and filtered. The filtrate was evaporated in vacuo. The resulting residue was recrystallized in dichloromethane-ethyl ether to afford the title compound. 1H NMR (500 MHz; DMSO-d6) δ 11.30 (d, 1H), 8.34 (d, 1H), 8.26 (m, 1H), 7.71 (m, 2H), 7.34 (s, 0.6H), 7.27 (s, 0.4H), 4.67 (s, 1.2H), 4.57 (s, 0.8H), 4.42 (s, 0.8H), 4.27 (s, 1.2H), 4.21 (t, 1.2H), 4.07 (t, 0.8H), 3.95 (t, 1.2H), 3.85 (t, 0.8H), 1.74 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  4. washthe solution was washed with water, saturated sodium bicarbonate solution, 1N HCl solution, and saline
  5. dry with materialThe resulting solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customThe resulting residue was recrystallized in dichloromethane-ethyl ether

Sources & evidence

ORD record
ord-16254e1dea2040f3a8ce4a2d79396390
Source dataset
uspto-grants-2006_12
Patent number
US07145006B2

Reaction notes

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