Methylamine → 5-(4-chlorophenyl)-6-cyclohexyl-N-methyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxamide

HRID 505815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505815
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[C:11]3[CH:22]=[C:23]([C:25]([OH:27])=O)[S:24][C:10]=3[C:9]=2[CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:4][CH:3]=1.CN.C[CH2:37][N:38](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[O:15])[C:11]3[CH:22]=[C:23]([C:25]([NH:38][CH3:37])=[O:27])[S:24][C:10]=3[C:9]=2[CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113177625-(4-Chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

Produkt 1

HCID 684698575-(4-chlorophenyl)-6-cyclohexyl-N-methyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution (0.02 M) of 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid in DCM at RT was treated with methylamine (2 N solution in THF, 1.5 eq.), DIEA (3 eq.) and HATU (2 eq.). The mixture was stirred at RT for 2 h, then it was diluted with DCM and washed sequentially with aqueous HCl (0.1 N), aqueous NaHCO3 (saturated solution) and dried. Evaporation of the solvent under reduced pressure gave a residue which was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 10 micron, 19×100 mm; flow: 20 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 50% A isocratic for 1 min then linear to 20% A in 9 min) to afford the title compound (74%) as a solid.

Aufarbeitung

  1. washwashed sequentially with aqueous HCl (0.1 N), aqueous NaHCO3 (saturated solution)
  2. customdried
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a residue which
  5. customwas purified by RP-HPLC (Conditions
  6. wait50% A isocratic for 1 min then linear to 20% A in 9 min

Quellen und Nachweise

ORD-Eintrag
ord-f4dea267908b49b98090b09e9d512698
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781431B2

Notizen zur Reaktion

Wird geladen…