Dabco → HCID 59702095, compound

HRID 902484Notes

Reaction equation

HRID 902484 reaction equation
N12CCN(CC1)CC2.[CH2:9]([O:11][C:12]([C:14]1[C:19](=[O:20])[NH:18][C:17]2[CH:21]=[CH:22][S:23][C:16]=2[C:15]=1Cl)=[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:19](=[O:20])[NH:18][C:17]2[CH:21]=[CH:22][S:23][C:16]=2[C:15]=1[N:28]1[CH2:29][CH2:30][N:25]([C:31]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[O:32])[CH2:26][CH2:27]1)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 9237DabcoHCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 15565856HCID 15565856, compound

Product 1

HCID 59702095HCID 59702095, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

1,4-Diazabicyclo[2.2.2]octane (224 mg, 2 mmol) was added to a solution of 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (4) (240 mg, 1 mmol) and piperazin-1-yl-thiophene-2-yl-methanone (215 mg, 1.1 mmol) in dry DMA. The solution was heated at 120° C. for 2 h. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried to yield 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (400 mg, 96%) as white solids. MP 252° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.27 (t, J=7.2 Hz, 3H), 3.31 (m, 4H), 3.77 (m, 4H), 4.24 (q, J=7.2 Hz, 2H), 6.97 (d, J=5.6 Hz, 1H), 7.15 (dd, J=3.6, 4.8 Hz, 1H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.80 (dd, J=1.2, 4.8 Hz, 1H), 7.96 (d, J=5.6 Hz, 1H), 12.10 (s, 1H) ppm; MS m/z=418 amu (M++1).

Workup

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. customdried

Sources & evidence

ORD record
ord-e1538a4ab4d241988c395753eed52ae4
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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