Potassium tert-butoxide → 2-Chloro-4-(4-cyclopropyl-3-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2-thia-3,6-diaza-naphthalen-8-yl)-benzonitrile

HRID 391333Notes

Reaction equation

HRID 391333 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([Cl:16])[CH:9]=2)=[CH:6][N:5]=[CH:4][C:3]=1[CH:17]([CH:24]1[CH2:26][CH2:25]1)[N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20].CC([O-])(C)C.[K+]>C1COCC1.CS(C)=O>[Cl:16][C:10]1[CH:9]=[C:8]([C:7]2[CH:6]=[N:5][CH:4]=[C:3]3[C:2]=2[CH2:22][S:19](=[O:21])(=[O:20])[N:18]([CH3:23])[CH:17]3[CH:24]2[CH2:26][CH2:25]2)[CH:13]=[CH:12][C:11]=1[C:14]#[N:15]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59578406N-((4-chloro-5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)-N-methylmethanesulfonamide

Product 1

HCID 498210552-Chloro-4-(4-cyclopropyl-3-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2-thia-3,6-diaza-naphthalen-8-yl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of N-((4-chloro-5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)-N-methylmethanesulfonamide (51 mg, 0.124 mmol) in THF (10 mL) and DMSO (0.1 mL) was added 1M KOtBu in THF (0.37 mL, 0.37 mmol), and the mixture was heated to 65° C. for 10 min under microwave irradiation. The mixture was quenched with MeOH (2 mL) and concentrated. The residue was purified by Xbridge C18 eluting with 20-100% ACN-water to give 2-chloro-4-(4-cyclopropyl-3-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2-thia-3,6-diaza-naphthalen-8-yl)-benzonitrile

Workup

  1. customThe mixture was quenched with MeOH (2 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by Xbridge
  4. washC18 eluting with 20-100% ACN-water

Sources & evidence

ORD record
ord-87d16b5dc04346b88f3f29361cc6bc3b
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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