Oxalyl chloride → HCID 178484067, Verbindung

HRID 2118246

Reaktionsgleichung

Reaktionsgleichung von HRID 2118246
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]2)[CH3:9])=[N:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[CH:26]1([NH2:29])[CH2:28][CH2:27]1>C(Cl)Cl.CN(C=O)C>[CH:26]1([NH:29][C:17]([C@H:14]2[CH2:13][CH2:12][C@H:11]([CH2:10][N:8]([C:5]3[N:6]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=3)[CH3:9])[CH2:16][CH2:15]2)=[O:19])[CH2:28][CH2:27]1

Komponenten

6

Edukt 3

HCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 178484083HCID 178484083, Verbindung

Produkt 1

HCID 178484067HCID 178484067, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 0.50 g (1.52 mmol) of trans-4-{[(5-bromo-pyrimidin-2-yl)-methyl-amino]-methyl}-cyclohexanecarboxylic acid in 4.5 mL of CH2Cl2 was treated at RT with 1 drop of DMF followed by 0.14 mL (1.68 mmol, 1.1 eq) of oxalyl chloride within 5 min, and stirring was continued for 90 min. The solution was evaporated, the residue was redissolved in CH2Cl2 and added dropwise to a solution of 2.14 mL (30.47 mmol, 20 eq) of cyclopropylamine in 3 mL of CH2Cl2 at 0° C. The reaction was warmed to RT and left for 3 h, then partitioned between Et2O (×3)/aqueous 10% NaHCO3, washed once with aqueous 10% NaHCO3, dried over Na2SO4 and evaporated to yield 0.55g (99%) of trans-4-{[(5-bromo-pyrimidin-2-yl)-methyl-amino]-methyl}-cyclohexanecarboxylic acid cyclopropylamide, MS: 367 (MH+, 1Br).

Aufarbeitung

  1. customThe solution was evaporated
  2. dissolutionthe residue was redissolved in CH2Cl2
  3. waitleft for 3 h
  4. custompartitioned between Et2O (×3)/aqueous 10% NaHCO3
  5. washwashed once with aqueous 10% NaHCO3
  6. dry with materialdried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f4233a164c174bc590a367d2ed9808bd
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442791B2

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