4-Methylmorpholine → HCID 73856345, compound

HRID 2213579Notes

Reaction equation

HRID 2213579 reaction equation
C[N:2]1CCOCC1.[C:8]1([CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH:31]=[C:32]3[S:36][C:35](=[S:37])[N:34]([CH2:38][C:39]([OH:41])=O)[C:33]3=[O:42])[CH:19]=[CH:20][C:21]=2[O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.ON1C2N=CC=CC=2N=N1.[Cl-].[NH4+].Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[C:8]1([CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH:31]=[C:32]3[S:36][C:35](=[S:37])[N:34]([CH2:38][C:39]([NH2:2])=[O:41])[C:33]3=[O:42])[CH:19]=[CH:20][C:21]=2[O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3010538HCID 3010538, compound

Product 1

HCID 73856345HCID 73856345, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-methylmorpholine (0.17 mL, 1.58 mmol, 4 eq) was added to a solution of 5-[[3-(phenylmethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (200 mg, 0.40 mmol, 1 eq), 1-hydroxy-7-azabenzotriazole (108 mg, 0.79 mmol, 2 eq) and ammonium chloride (42 mg, 0.79 mmol, 2 eq) in N,N-dimethylformamide (5 mL). To this mixture was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (152 mg, 0.79 mmol, 2 eq) and the reaction mixture was stirred for 48 h. It was diluted with ethyl acetate (50 mL), and the organic solution washed with 1M HCl, (3×100 mL), then water (100 mL), dried over sodium sulfate and concentrated in vacuo. A yellow powder precipitated from the concentrate which was collected by filtration, washed with ethyl acetate and petroleum ether and dried to give the product (185 mg, 93%) mp 212–214° C.: 1H NMR (d6 DMSO) 7.76 (s, 1H, C═C— 7.72 (broad s, 2H, exchanges with D2O, NH2), 5.16 (s, 2H, OCH2Ph), 4.60 (s, 2H, CH2CO2H), 4.30 (t, 2H, J 6.4 Hz, OCH2CH2), 3.07 (t, 2H, J 6.4 Hz, OCH2CH2).

Workup

  1. washthe organic solution washed with 1M HCl, (3×100 mL),
  2. dry with materialwater (100 mL), dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customA yellow powder precipitated from the
  5. concentrationconcentrate which
  6. filtrationwas collected by filtration
  7. washwashed with ethyl acetate and petroleum ether
  8. customdried

Sources & evidence

ORD record
ord-bb0948b3b45e45db9e654ee457269336
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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