2-Methoxyethanol → HCID 86626796, compound

HRID 604036Notes

Reaction equation

HRID 604036 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[N:26]([CH2:37][CH3:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]1[N:13]=[CH:12][C:11]([OH:14])=[CH:10][N:9]=1.[CH3:48][O:49][CH2:50][CH2:51]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.[Cl-].[Na+].O>[F:47][C:2]([F:1])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:41]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[N:26]([CH2:37][CH3:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]1[N:9]=[CH:10][C:11]([O:14][CH2:51][CH2:50][O:49][CH3:48])=[CH:12][N:13]=1

Participants

8

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86626797HCID 86626797, compound

Product 1

HCID 86626796HCID 86626796, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 6-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-hydroxy-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-ethyl-amino]-hexanoate (120 mg) is dissolved in tetrahydrofuran (1 ml), and thereto are added 2-methoxyethanol (21 μl) and triphenylphosphine (69 mg), and thereto is added dropwise 40% diethyl azodicarboxylate in toluene (115 μl) under water-cooling, and the mixture is stirred at room temperature for 1 hour. To the reaction mixture is added a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (hexane:ethyl acetate=6:1) to give ethyl 6-{[2-({(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methoxy-ethoxy)-pyrimidin-2-yl]-amino}-methyl)-4-trifluoromethyl-phenyl]-ethyl-amino}-hexanoate (120 mg). MS (m/z): 739 [M+H]+

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by NH-silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-0dee74e937394ebe9875af334f763ef4
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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