Ethyl N-methylaminoacetate hydrochloride → HCID 14986923, compound

HRID 1493586Notes

Reaction equation

HRID 1493586 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:46])([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:37](OC4C=CC=CC=4)=[O:38])=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1)[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.Cl.C([O:50][C:51](=O)[CH2:52][NH:53][CH3:54])C.C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:46])([CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)[CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:25][CH2:26][N:27]([C:30]3[CH:31]=[CH:32][C:33]([N:36]4[C:51](=[O:50])[CH2:52][N:53]([CH3:54])[C:37]4=[O:38])=[CH:34][CH:35]=3)[CH2:28][CH2:29]2)=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 516892Sodium BicarbonateHCID 19830007HCID 19830007, compound

Product 1

HCID 14986923HCID 14986923, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(2,4-dichlorophenyl)-3-(4-[4-(4-phenoxycarbonylaminophenyl)piperazin-1-yl]phenoxy)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (see Preparation 2) (0.3 g, 0.45 mmole), sarcosine ethyl ester hydrochloride (0.09 g, 0.58 mmole), 4-(N,N-dimethylamino)pyridine (0.03 g, 0.24 mmole) and sodium bicarbonate (0.09 g, 1 mmole) in 1,4-dioxane (30 ml) was heated under reflux for 18 hours. After cooling, the mixture was diluted with water, extracted with ethyl acetate and the organic phase washed with brine. After drying over magnesium sulphate, the organic phase was concentrated under reduced pressure to yield a gum, which on trituration with ether gave a pale yellow solid (0.260 g). Purification of this solid material by flash chromatography on silica gel eluting with methylene chloride (90):isopropanol (10):acetic acid (0.2) yielded, after collection and evaporation of appropriate fractions, the desired product as a colourless solid, m.p. 213°-215° (0.13 g, 45%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washthe organic phase washed with brine
  6. dry with materialAfter drying over magnesium sulphate
  7. concentrationthe organic phase was concentrated under reduced pressure
  8. customto yield a gum, which on trituration with ether

Sources & evidence

ORD record
ord-a38039b22d4f4f279f6add31eba1da6c
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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