Chloroform → cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[2-[methyl(1-pyrrolidinylcarbonyl)amino]ethyl]-4-piperidinyl]-7-benzofurancarboxamide monohydrate

HRID 865398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865398
O.[NH2:2][C:3]1[C:8]2[CH2:9][CH2:10][O:11][C:7]=2[C:6]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][NH:23][CH3:24])[CH2:17][C@H:16]2[O:25][CH3:26])=[O:13])=[CH:5][C:4]=1[Cl:27].ClC(Cl)Cl.[N:32]1([C:37](Cl)=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]1>C(N(CC)CC)C>[OH2:11].[NH2:2][C:3]1[C:8]2[CH2:9][CH2:10][O:11][C:7]=2[C:6]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]([CH3:24])[C:37]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:38])[CH2:17][C@H:16]2[O:25][CH3:26])=[O:13])=[CH:5][C:4]=1[Cl:27]

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 709371-Pyrrolidinecarbonyl chlorideHCID 67704506cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[2-(methylamino)ethyl]-4-piperidinyl]-7-benzofurancarboxamide monohydrate

Produkt 1

HCID 67704495cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[2-[methyl(1-pyrrolidinylcarbonyl)amino]ethyl]-4-piperidinyl]-7-benzofurancarboxamide monohydrateAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (ice-bath) mixture of 3.8 parts of cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[2-(methylamino)ethyl]-4-piperidinyl]-7-benzofurancarboxamide mono-hydrate in 104.3 parts of trichloromethane were added 1.3 parts of 1-pyrrolidinecarbonyl chloride. After stirring for 15 min. at 0° C., there were added dropwise 1.31 parts of N,N-diethylethanamine, keeping the temperature below 10° C. Stirring was continued for 20 hours at room temperature. The reaction mixture was washed with water, dried, filtered and evaporated. The residue was crystallized from acetonitrile (to which some water was added). The product was filtered off at 0° C. and dried in vacuo at 40° C., yielding 3.3 parts (73.6%) of cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[2[methyl(1-pyrrolidinylcarbonyl)amino]ethyl]-4-piperidinyl]-7-benzofurancarboxamide monohydrate; mp. 112.0° C. (comp. 43).

Aufarbeitung

  1. temperatureTo a cooled
  2. customthe temperature below 10° C
  3. stirringStirring
  4. waitwas continued for 20 hours at room temperature
  5. washThe reaction mixture was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from acetonitrile (to which some water
  10. additionwas added)
  11. filtrationThe product was filtered off at 0° C.
  12. customdried in vacuo at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-18af384c176b48beb76437659115d1e7
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565582

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