Triethylamine → HCID 9868291, compound

HRID 1825663Notes

Reaction equation

HRID 1825663 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[O:17][C:16]([C:19](O)=[O:20])=[CH:15][C:14]3=[O:22])[CH2:5][CH2:4]1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.[NH2:40][C:41]1[CH:46]=[CH:45][C:44]([N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)=[CH:43][C:42]=1O>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:2][N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[O:17][C:16]([C:19]([NH:40][C:41]2[CH:42]=[CH:43][C:44]([N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[CH:45][CH:46]=2)=[O:20])=[CH:15][C:14]3=[O:22])[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 23533293HCID 23533293, compoundHCID 69271961HCID 69271961, compound

Product 1

HCID 9868291HCID 9868291, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

8-(4-methyl-1-piperazinyl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 1) (400 mg, 1.23 mmol) was suspended in anhydrous N,N-dimethylformamide (20 ml) and triethylamine (0.69 ml, 4.92 mmol) was added to give a clear solution. The following were added in order: 1-hydroxybenzotriazole (HOBt (205 mg, mol)), O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-pentamethylene-uronium tetrafluoroborate (TBTU (435 mg, 3.1 mmol)) then 4-(dimethylamino)pyridine (25 mg). After stirring for 5 min at room temperature, 4-(4-morpholinyl)aniline (Reference Example 21) (220 mg, mmol). The reaction stirred overnight at room temperature. The solution was concentrated in vacuo, the remains were partitioned between chloroform/saturated sodium bicarbonate, extracted (×3) with chloroform, dried (MgSO4) and concentrated in vacuo to give the crude product.

Workup

  1. customto give a clear solution
  2. additionThe following were added in order
  3. stirringThe reaction stirred overnight at room temperature
  4. concentrationThe solution was concentrated in vacuo
  5. customthe remains were partitioned between chloroform/saturated sodium bicarbonate
  6. extractionextracted (×3) with chloroform
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b63d2b67e5fc4aa88c71c2880eb0cef4
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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