Lawesson's reagent → HCID 9977271, compound

HRID 2304498Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[C:9]1[C:15]1[CH:27]=[CH:26][C:18]2[NH:19][C:20](=O)[O:21][C:22]([CH3:24])([CH3:23])[C:17]=2[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>C1(C)C=CC=CC=1>[C:13]([C:12]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]([C:15]2[CH:27]=[CH:26][C:18]3[NH:19][C:20](=[S:37])[O:21][C:22]([CH3:24])([CH3:23])[C:17]=3[CH:16]=2)=[CH:10][CH:11]=1)#[N:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To 2-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-5-cyano-pyrrole-1-carboxylic acid tert-butyl ester (1.3 g, 35 mmol, 1 eq) in toluene (130 mL) was added Lawesson's reagent (1.58 g, 3.9 mmol, 1.1 eq) and the reaction mixture was heated to 80° C. for 2 h. The solvent was removed in vacuo and the residue was dissolved in acetone/dichloromethane and adsorbed onto silica gel. Purification by flash column chromatography (10% ethyl acetate/hexane) gave the product (0.51 g, 38%) as yellow crystals. 1H NMR (DMSO-d6) δ1.35 (s, 9H), 1.64 (s, 6H), 6.47 (d, 1H, J=3.6 Hz), 7.07 (d, 1H, J=8.1 Hz), 7.32 (d, 1H, J=3.6 Hz), 7.37 (dd, 1H, J=1.8, 8.1 Hz), 7.43 (d, 1H, J=1.8 Hz), 12.28 (s, 1H); MS (ESI) [M−H]−=382; Anal. Calcd. For C20H21N3O3S: C, 62.64; H, 5.52; N, 10.96. Found: C, 62.53; H, 5.6; N, 10.87.

Workup

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in acetone/dichloromethane
customPurification by flash column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-49c5a32267954193a663ccbf756c0500
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436929B1

Reaction notes

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