Acryloyl chloride → HCID 136983767, Verbindung

HRID 64296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64296
[NH2:1][CH2:2][CH:3]1[N:8]2[N:9]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:11]([C:12]([NH2:14])=[O:13])=[C:7]2[NH:6][CH2:5][CH2:4]1.[C:28](Cl)(=[O:31])[CH:29]=[CH2:30]>C(Cl)Cl.CCN(CC)CC>[C:28]([NH:1][CH2:2][CH:3]1[N:8]2[N:9]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:11]([C:12]([NH2:14])=[O:13])=[C:7]2[NH:6][CH2:5][CH2:4]1)(=[O:31])[CH:29]=[CH2:30]

Komponenten

5

Edukt 2

HCID 13140Acryloyl chlorideHCID 1369280997-(Aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

Produkt 1

HCID 136983767HCID 136983767, VerbindungAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-(aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide (125 mg, 0.344 mmol) in 5 mL of DCM was added Et3N (four drops) and acryloyl chloride (46.5 mg, 0.52 mmol). After stirring at rt for 30 mins. The mixture was partitioned between water (10 mL) and DCM (5 mL). The organic layer was concentrated and purified by pre-TLC (DCM/MeOH=20/1) to give 40 mg (28%) of product. 1H NMR (400 MHz, DMSO-d6) δ 8.37 (t, J=6.0 Hz, 1H), 7.59 (d, J=8.8 Hz, 2H), 7.54-7.43 (m, 2H), 7.25 (t, J=7.6 Hz, 1H), 7.16-7.11 (m, 4H), 6.76 (s, 1H), 6.33 (dd, J=10.1, 17.0 Hz, 1H), 6.18 (dd, J=1.9, 17.0 Hz, 1H), 5.69 (dd, J=1.9, 10.1 Hz, 1H), 4.28-4.22 (m, 1H), 3.92-3.80 (m, 1H), 3.50-3.30 (m, 3H), 2.14-1.94 (m, 2H). MS (ESI) m/e [M+1]+ 417.9.

Aufarbeitung

  1. customThe mixture was partitioned between water (10 mL) and DCM (5 mL)
  2. concentrationThe organic layer was concentrated
  3. custompurified by pre-TLC (DCM/MeOH=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-68d81d2671e04ae68e47944ebc088e41
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

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