Diisopropylethylamine → (2-{4-[(2-Chloro-acetyl)-methyl-amino]-benzoylamino}-cyclohexyl)-carbamic acid tert-butyl ester

HRID 1241895

Reaktionsgleichung

Reaktionsgleichung von HRID 1241895
[Cl:1][CH2:2][C:3]([N:5]([CH3:15])[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)=[O:4].[C:16]([O:20][C:21](=[O:30])[NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[NH2:29])([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:16]([O:20][C:21](=[O:30])[NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[NH:29][C:10](=[O:12])[C:9]1[CH:8]=[CH:7][C:6]([N:5]([C:3](=[O:4])[CH2:2][Cl:1])[CH3:15])=[CH:14][CH:13]=1)([CH3:19])([CH3:17])[CH3:18]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 3268011tert-Butyl (2-aminocyclohexyl)carbamateHCID 7010325N-Methyl-4-(2-chloroacetamido)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 69666167(2-{4-[(2-Chloro-acetyl)-methyl-amino]-benzoylamino}-cyclohexyl)-carbamic acid tert-butyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Part A. 4-[(2-Chloro-acetyl)-methyl-amino]-benzoic acid (0.23 g, 1.0 mmol.) was stirred in DMF (2 mL) at RT under N2. (2-Amino-cyclohexyl)-carbamic acid tert-butyl ester (0.21 g, 1.0 mmol), HATU (0.57 g, 1.5 eq) and DIEA (0.5 mL, 2.9 eq) were added. The mixture was stirred at RT for 30 min. It was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to dryness to give (2-{4-[(2-chloro-acetyl)-methyl-amino]-benzoylamino}-cyclohexyl)-carbamic acid tert-butyl ester (0.40 g, yield: 95%).

Aufarbeitung

  1. customIt was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-94731066281a4fa0b2519b116f9a915f
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115627B2

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