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 742824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 742824
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 monohydrate 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-364a5575619f45558ddb4913c969b199
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554772

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