Lawesson's reagent → HCID 86607618, compound

HRID 2357690Notes

Reaction equation

[CH:1]1([NH:4][C:5](=O)[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>C1COCC1>[CH:1]1([NH:4][C:5](=[S:39])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-cyclopropyl-4-methyl-3-(1-morpholinophthalazin-6-yl)benzamide (85 mg, 0.22 mmol) and Lawesson's reagent (97 mg, 0.24 mmol) in 1 mL THF was heated at 150° C. for 10 min in a microwave oven. Volatile solvents were removed under reduced pressure and the brown residue was purified on an ISCO column (12 g, eluted with 1-10% MeOH in ethyl acetate) to provide N-cyclopropyl-4-methyl-3-(l-morpholinophthalazin-6-yl)benzothioamide as a yellow solid. Found MS (ESI+) m/z: 405.3 (M+1).

Workup

customVolatile solvents were removed under reduced pressure
customthe brown residue was purified on an ISCO column (12 g, eluted with 1-10% MeOH in ethyl acetate)

Sources & evidence

ORD record: ord-4b96e46f5de547b89fea10e922d65b04
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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