Triethylamine → alpha-[N-(Acetamido)amino]-N-[4-(5H-pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

HRID 1456147

Reaktionsgleichung

Reaktionsgleichung von HRID 1456147
Cl[CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][N:17]3[CH:25]=[CH:26][CH:27]=[C:16]3[CH2:15]2)=[O:13])=[CH:8][CH:7]=1)=[O:4].Cl.N[CH2:36][C:37]([NH2:39])=[O:38].C([N:42](CC)CC)C.CN1CCCN(C)C1=O>CO>[C:37]([NH:39][NH:42][CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][N:17]3[CH:25]=[CH:26][CH:27]=[C:16]3[CH2:15]2)=[O:13])=[CH:8][CH:7]=1)=[O:4])(=[O:38])[CH3:36]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 2723639Glycinamide hydrochlorideHCID 21837022alpha-Chloro-N-[4-(5H-pyrrolo[2,1-c][1,4)benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

Produkt 1

HCID 21837136alpha-[N-(Acetamido)amino]-N-[4-(5H-pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamideAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 0.14 g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide, 0.17 g of glycinamide HCl, 0.15 g of triethylamine, 3 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and 1 ml of methyl alcohol is heated at 75° C. for 2 days. The methyl alcohol is evaporated and the residue diluted with water. The resulting suspension is filtered and the precipitate washed with water. The solid is dissolved in ethyl acetate and washed with saturated NaHCO3, brine and dried with Na2SO4. The mixture is filtered and the filtrate evaporated in vacuo to a residue which is stirred with ether-hexanes to give 0.13 g of tan solid. MS(CI): 494(M+H).

Aufarbeitung

  1. customThe methyl alcohol is evaporated
  2. additionthe residue diluted with water
  3. filtrationThe resulting suspension is filtered
  4. washthe precipitate washed with water
  5. dissolutionThe solid is dissolved in ethyl acetate
  6. washwashed with saturated NaHCO3, brine
  7. dry with materialdried with Na2SO4
  8. filtrationThe mixture is filtered
  9. customthe filtrate evaporated in vacuo to a residue which

Quellen und Nachweise

ORD-Eintrag
ord-cbabe9a3d68a4cab8516ec868ba4a235
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843944

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