Dabco → HCID 59702104, compound

HRID 902510Notes

Reaction equation

N12CCN(CC1)CC2.[CH2:9]([O:11][C:12]([C:14]1[C:15](=[O:24])[NH:16][C:17]2[C:21]([C:22]=1Cl)=[CH:20][S:19][CH:18]=2)=[O:13])[CH3:10].[N:25]1([C:31]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CC(N(C)C)=O>[CH2:9]([O:11][C:12]([C:14]1[C:15](=[O:24])[NH:16][C:17]2[C:21]([C:22]=1[N:28]1[CH2:29][CH2:30][N:25]([C:31]([C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)=[O:32])[CH2:26][CH2:27]1)=[CH:20][S:19][CH:18]=2)=[O:13])[CH3:10]

Participants

Conditions

Temperature: 110 °C

Procedure

1,4-Diazabicyclo[2.2.2]octane (2.07 g, 10.16 mmol) was added to a solution of 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester (39) (2.4 g, 9.24 mmol) and piperazin-1-yl-thiophene-2-yl-methanone (1.99 g, 10.16 mmol) in dry DMA. The solution was heated at 110° C. for 3 h. The solution was cooled and the solvent was distilled. The residue was suspended in water, sonicated briefly, and filtered. The solids were washed by excess water and dried to yield 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester (3.47 g, 90%) as white solids. MP 282° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.27 (t, J=7.2 Hz, 3H), 3.27 (m, 4H), 3.77 (m, 4H), 4.24 (q, J=7.2 Hz, 2H), 6.86 (d, J=3.6 Hz, 1H), 7.15 (dd, J=3.6, 5.2 Hz, 1H), 7.46 (dd, J=1.2, 3.6 Hz, 1H), 7.80 (dd, J=1.2, 4.8 Hz, 1H), 8.02 (d, J=3.2 Hz, 1H), 11.30 (s, 1H) ppm; MS m/z=418 amu (M++1).

Workup

temperatureThe solution was cooled
distillationthe solvent was distilled
customsonicated briefly
filtrationfiltered
washThe solids were washed by excess water
customdried

Sources & evidence

ORD record: ord-61b11c89a26f48c79f648a742dadbd85
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365200B2

Reaction notes

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