Water → HCID 86618700, compound

HRID 2239379Notes

Reaction equation

HRID 2239379 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:17][C:11]3[C:12](=[O:16])[NH:13][N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:25][C:26]1[N:31]=[C:30]([O:32][CH2:33][C@H:34]2[CH2:38][CH2:37][CH2:36][N:35]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:29]=[CH:28][CH:27]=1)(=O)=O.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:17][C:11]3[C:12](=[O:16])[N:13]([CH2:25][C:26]4[N:31]=[C:30]([O:32][CH2:33][C@H:34]5[CH2:38][CH2:37][CH2:36][N:35]5[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:29]=[CH:28][CH:27]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 115798042-(4-Chlorophenyl)thieno[2,3-d]pyridazin-7(6H)-oneHCID 86618699HCID 86618699, compound

Product 1

HCID 86618700HCID 86618700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(4-Chlorophenyl)thieno[2,3-d]pyridazin-7(6H)-one (285 mg, 1.1 mmol) was added to dry DMF (5 mL) and NaH (71 mg, 55% in mineral oil, 1.6 mmol) was added in small potions and stirred 10 min. tert-butyl (2R)-2-{[(6-{[(methylsulfonyl)oxy]methyl}pyridin-2-yl)oxy]methyl}pyrrolidine-1-carboxylate (420 mg, 1.1 mmol) dissolved in dry DMF (3 mL) was added drop wise and the reaction mixture was stirred at ambient temperature for 3 h. Water was added and the aqueous phase was extracted three times with DCM. The organic phase was evaporated and purified by flash chromatography using a gradient of EtOAc/heptane to give the title compound as a yellow solid. Yield: 380 mg (63%). 1H NMR (399.961 MHz, CDCl3) δ 8.22 (s, 1H), 7.64 (d, J=8.7 Hz, 2H), 7.53-7.42 (m, 4H), 6.72 (d, J=7.3 Hz, 1H), 6.61 (d, J=8.1 Hz, 1H), 5.48 (s, 2H), 4.41-4.01 (m, 3H), 3.43-3.25 (m, 2H), 1.97-1.74 (m, 4H), 1.42 (s, 9H). MS (ESI+) 553.3 (M+1H+)

Workup

  1. additionwas added in small potions
  2. additionwas added drop wise
  3. extractionthe aqueous phase was extracted three times with DCM
  4. customThe organic phase was evaporated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-be12e2159f664261bdfe5574a8bdc5cb
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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