Potassium Carbonate → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-methylthieno[2,3-b]pyrazine-6-carboxamide

HRID 1184836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184836
Cl[C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=4)[CH:17]=[CH:16][C:15]=3[CH3:34])=[O:12])[S:8][C:5]2=[N:6][CH:7]=1.[C:35](=O)([O-])[O-].[K+].[K+]>C1COCC1.[NH4+].[Cl-].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:18]1[CH:17]=[CH:16][C:15]([CH3:34])=[C:14]([NH:13][C:11]([C:9]2[S:8][C:5]3=[N:6][CH:7]=[C:2]([CH3:35])[N:3]=[C:4]3[CH:10]=2)=[O:12])[CH:19]=1)=[O:33])([CH3:30])[CH3:29])#[N:32]

Komponenten

6

Edukt 2

HCID 11430Potassium CarbonateHCID 547564232-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

Produkt 1

HCID 67125588N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-methylthieno[2,3-b]pyrazine-6-carboxamideAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 24 (40 mg, 0.082 mmol), potassium carbonate (22.56 mg, 0.163 mmol) and 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) (5.91 mg, 8.16 μmol) in THF was heated to 60° C. for 6 h. The reaction mixture was poured in NH4Cl solution and extracted twice with EtOAc. Organic layer was washed with water, brine, dried and evaporated. Crude product triturated twice with CH2Cl2 to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-methylthieno[2,3-b]pyrazine-6-carboxamide 251 (5 mg, 13%). NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.26 (s, 3H), 2.68 (s, 3H), 7.31 (d, J=8.2 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.66 (d, J=8.6 Hz, 1H), 7.75 (m, 1H), 7.87 (d, J=2.3 Hz, 1H), 7.96 (d, J=7.4 Hz, 1H), 8.06 (s, 1H), 8.47 (s, 1H), 8.67 (s, 1H), 10.40 (s, 1H), 10.54 (br s, 1H). (m/z)=470 (M+H)+.

Aufarbeitung

  1. extractionextracted twice with EtOAc
  2. washOrganic layer was washed with water, brine
  3. customdried
  4. customevaporated
  5. customCrude product triturated twice with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-684405cc8ee8420ab4c6d5ac3436ab8e
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669256B2

Notizen zur Reaktion

Wird geladen…