Diisopropylethylamine → 9-{[4-(Ethyloxy)phenyl]sulfonyl}-2-methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one

HRID 1427164Notes

Reaction equation

HRID 1427164 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13](=[O:14])[N:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH:7]3[C:6]=2[N:15]=1.CCN(C(C)C)C(C)C.[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)[CH3:26]>C(Cl)Cl>[CH2:25]([O:27][C:28]1[CH:29]=[CH:30][C:31]([S:34]([N:11]2[CH2:10][CH2:9][N:8]3[C:13](=[O:14])[C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[N:15][C:6]=4[CH:7]3[CH2:12]2)(=[O:36])=[O:35])=[CH:32][CH:33]=1)[CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 36883344-Ethoxybenzene-1-sulfonyl chlorideHCID 705575122-Methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one2×

Product 1

HCID 575242899-{[4-(Ethyloxy)phenyl]sulfonyl}-2-methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-oneYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-methyl-8,9,10,10a-tetrahydropyrido[2′,3′:3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one (may be prepared as described in Intermediate 8; 70 mg) in DCM (5 mL) was added DIPEA (0.241 mL, 1.378 mmol). To this was added 4-(ethyloxy)benzenesulfonyl chloride (80 mg) and this was allowed to stir at room temperature for 30 minutes. The reaction mixture was partitioned between DCM and saturated sodium bicarbonate solution in a hydrophobic frit. The aqueous layer was re-extracted with DCM. The combined organic phases were evaporated to an orange oil. The residue was purified by chromatography (25S silica cartridge) eluting with 0-5% methanol in DCM over 12 column volumes. The clean fractions were combined and evaporated to give the title compound as a white foam (84 mg).

Workup

  1. customThe reaction mixture was partitioned between DCM and saturated sodium bicarbonate solution in a hydrophobic frit
  2. extractionThe aqueous layer was re-extracted with DCM
  3. customThe combined organic phases were evaporated to an orange oil
  4. customThe residue was purified by chromatography (25S silica cartridge)
  5. washeluting with 0-5% methanol in DCM over 12 column volumes
  6. customevaporated

Sources & evidence

ORD record
ord-bbf8b54f7e754a159771e67e804cd99a
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

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