p-Methoxyphenylthionophosphine sulfide → 7-Chloro-6-pyridin-3-yl-8-thiocarbamoyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester

HRID 857899Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[C:15]([Cl:20])[C:16]([C:17](=O)[NH2:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P(=S)=[S:36])=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[C:15]([Cl:20])[C:16]([C:17](=[S:36])[NH2:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred suspension of 8-carbamoyl-7-chloro-6-pyridin-3-yl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (486 mg, Reference Example 2b) in toluene (25 mL) was treated with 4-methoxyphenylthionophosphine sulfide dimer (513 mg). After stirring at 80° C. for 2 hours the reaction mixture was allowed to cool to room temperature and then evaporated. The residue was subjected to column chromatography on silica eluting with dichloromethane, then with a mixture of methanol and dichloromethane (1:99, v/v) and then with a mixture of methanol and dichloromethane (1:49, v/v) to give the title compound (129 mg) as a off white solid, m.p. 220–221° C. [Elemental Analysis: C, 54.79; H, 5.10; N, 13.86%. Calculated for C18H21ClN4O2S: C, 55.03; H, 5.39; N, 14.26%].

Workup

temperatureto cool to room temperature
customevaporated
additionwith a mixture of methanol and dichloromethane (1:99, v/v)
additionwith a mixture of methanol and dichloromethane (1:49, v/v)

Sources & evidence

ORD record: ord-a0a8f5ec5cf142af830299b5b382fd82
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148215B2

Reaction notes

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