4-Methylmorpholine → HCID 11305076, compound

HRID 602322Notes

Reaction equation

HRID 602322 reaction equation
O.ON1C2C=CC=CC=2N=N1.[Cl:12][C:13]1[S:17][C:16]([C:18]([OH:20])=O)=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.[O:40]=[C:41]1[CH2:46][O:45][CH2:44][CH2:43][N:42]1[C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:54]([CH:56]2[CH2:60][CH2:59][CH2:58][NH:57]2)=[O:55])=[CH:49][CH:48]=1>CN(C)C=O>[O:40]=[C:41]1[CH2:46][O:45][CH2:44][CH2:43][N:42]1[C:47]1[CH:48]=[CH:49][C:50]([NH:53][C:54]([C@H:56]2[CH2:60][CH2:59][CH2:58][N:57]2[C:18]([C:16]2[S:17][C:13]([Cl:12])=[CH:14][CH:15]=2)=[O:20])=[O:55])=[CH:51][CH:52]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66593134HCID 66593134, compound

Product 1

HCID 11305076HCID 11305076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.71 g (4.66 mmol) of 1-hydroxybenzotriazole hydrate, 0.76 g (4.66 mmol) of 5-chlorothiophenecarboxylic acid, 1.79 g (9.33 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 1.13 ml of N-methylmorpholine are added successively to a solution of 1.35 g (4.66 mmol) of N-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide in 30 ml of dimethylformamide, and the resultant solution is stirred at room temperature for 12 hours. The reaction solution is subsequently evaporated to dryness under reduced pressure, the residue is taken up in 10 ml of 5% sodium hydrogencarbonate solution, and the sodium hydrogencarbonate solution is extracted twice with 10 ml of ethyl acetate each time. After the combined organic phases have been dried over sodium sulfate and the solvent has been stripped off, the solid residue is triturated with 20 ml of diethyl ether, giving 1.2 g (59.4%) of “AB1”, ESI 434; m.p. 195°.

Workup

  1. customThe reaction solution is subsequently evaporated to dryness under reduced pressure
  2. extractionthe sodium hydrogencarbonate solution is extracted twice with 10 ml of ethyl acetate each time
  3. dry with materialAfter the combined organic phases have been dried over sodium sulfate
  4. customthe solid residue is triturated with 20 ml of diethyl ether
  5. customgiving 1.2 g (59.4%) of “AB1”, ESI 434

Sources & evidence

ORD record
ord-0952af2cb0ee4f91974b13514b71cea9
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

Loading…