Dichloromethane → HCID 60169549, Verbindung

HRID 536597

Reaktionsgleichung

Reaktionsgleichung von HRID 536597
[C:1]([NH2:5])([CH3:4])(C)C.C(OC([N:13]1CC[C:16](=O)[CH2:15][C@H:14]1C(O)=O)=O)(C)(C)C.[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[C:28]([CH:32]=1)[C:29]([OH:31])=O.CC[N:41]([CH:45]([CH3:47])C)[CH:42]([CH3:44])[CH3:43].C(P1(=O)OP(CCC)(=O)OP([CH2:62][CH2:63][CH3:64])(=O)O1)CC.C(Cl)[Cl:67]>>[Cl:67][C:15]1[CH:16]=[CH:4][C:1]([NH:5][CH2:44][C@H:42]2[N:41]([C:29]([C:28]3[CH:32]=[C:24]([CH3:23])[CH:25]=[CH:26][C:27]=3[C:33]3[N:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[O:31])[CH2:45][CH2:47][C:62]3([CH2:63][CH2:64]3)[CH2:43]2)=[N:13][CH:14]=1

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 445172645-Methyl-2-(pyrimidin-2-yl)benzoic acidHCID 66848353(S)-1-Boc-4-oxopiperidine-2-carboxylic acid tert-butylamine salt

Produkt 1

HCID 60169549HCID 60169549, Verbindung

Versuchsvorschrift

Alternatively Compound 13 was obtained by the following procedure: 5-methyl-2-(pyrimidin-2-yl)benzoic acid (428 mg, 2 mmol; prepared according to WO 2008147518), intermediate 34 (500 mg, 2 mmol) and DIPEA (0.65 ml) were dissolved in DCM (5 ml) at 0° C., then T3P (50% in DCM, 1.5 g) was added. The mixture is stirred at reflux for 8 hours then at RT overnight. The reaction was washed with NaOH 1M and water, dried (Na2SO4) and evaporated. The crude was purified by silica gel column chromatography (DCM to DCM/MeOH=95/05). 180 mg of the desired compound were isolated.

Aufarbeitung

  1. temperatureat reflux for 8 hours
  2. customat RT
  3. customovernight
  4. washThe reaction was washed with NaOH 1M and water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude was purified by silica gel column chromatography (DCM to DCM/MeOH=95/05)

Quellen und Nachweise

ORD-Eintrag
ord-b24d643e62b54fb8942e4316b1d777d7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859608B2

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