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2,6-Dimethylbenzoic acid → 2,6-Dimethyl-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]benzamide

HRID 20844
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 20844
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=O.[NH2:12][CH:13]([C:20]1(CN)[CH2:24][CH2:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:27][N:28](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCN(C(C)C)C(C)C>[CH3:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[C:3]=1[C:4]([NH:12][CH:13]([C:20]1([NH:28][CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:6]
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Komponenten

6

Edukt 3

HCID 124392,6-Dimethylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57444874{[Amino(phenyl)methyl]cyclopentyl}methylamine

Produkt 1

HCID 115228862,6-Dimethyl-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]benzamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dimethylbenzoic acid (0.100 g; 0.668 mmol) in DMF (5 ml) and DIPEA (0.12 ml) was added {[amino(phenyl)methyl]cyclopentyl}methylamine D31 enantiomer 2 (0.124 g; 0.608 mmol) and HATU (0.254 g; 0.668 mmol). The resulting mixture was allowed to stir at room temperature for 3 days and then the DMF was evaporated off under reduced pressure. Residual material was partitioned between ethyl acetate and water, washed with water and the organic layer was dried (Na2SO4) and evaporated. The residual material was dissolved in DCM (2 ml) and loaded onto an SCX cartridge. Washing with DCM, then methanol followed by elution with 1 M ammonia in methanol afforded the title product (155 mg; 76%). 1H NMR (CDCl3) δ: 1.3-1.8 (9H, m), 2.21 (3H, s), 2.28 (6H, s), 5.07 (1H, m), 7.0 (2H, m), 7.1-7.4 (7H, m). Mass Spectrum (Electrospray LC/MS). Found 337 (MH+). C22H28N2O requires 336. Ret. time: 1.86 min.

Aufarbeitung

  1. customthe DMF was evaporated off under reduced pressure
  2. customResidual material was partitioned between ethyl acetate and water
  3. washwashed with water
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residual material was dissolved in DCM (2 ml)
  7. washWashing with DCM
  8. washmethanol followed by elution with 1 M ammonia in methanol

Quellen und Nachweise

ORD-Eintrag
ord-4d7b6c3ca3c241229878f9f0254ed117
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07745642B2

Notizen zur Reaktion

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