O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 67064333, Verbindung

HRID 1256379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256379
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=[C:9]([NH2:16])[CH:8]=2)[CH2:3][CH2:2]1.[CH3:17][O:18][C:19]([C:21]1([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)[CH2:23][CH2:22]1)=[O:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=[C:9]([NH:16][C:28]([C:27]3[CH:26]=[CH:25][C:24]([C:21]4([C:19]([O:18][CH3:17])=[O:20])[CH2:22][CH2:23]4)=[CH:32][CH:31]=3)=[O:29])[CH:8]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 582073347-Morpholinopyrazolo[1,5-a]pyrimidin-5-amineHCID 588411094-(1-(Methoxycarbonyl)cyclopropyl)benzoic acid

Produkt 1

HCID 67064333HCID 67064333, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

7-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9A, 110 mg, 0.50 mmol) and 4-(1-(methoxycarbonyl)cyclopropyl)benzoic acid (110 mg, 0.50 mmol) were mixed in pyridine (3 ml). TBTU (160 mg, 0.50 mmol) was then added and the mixture was heated to 80° C. for 15 hours. After cooling to room temperature, additional TBTU (53 mg, 0.17 mmol) was added before the heating continued for another 6 hours. After cooling to room temperature, the reaction mixture was quenched with water and was then concentrated to dryness in vacuo. The crude product was purified by preparatory HPLC (35-55% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white powder (72 mg, 35% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.00 (s, 1 H), 8.10 (d, J=2.3 Hz, 1 H), 7.99 (d, J=8.3 Hz, 2 H), 7.49 (d, J=8.3 Hz, 2 H), 7.41 (s, 1 H), 6.38 (d, J=2.3 Hz, 1 H), 3.88-3.82 (m, 4 H), 3.78-3.70 (m, 4 H), 3.57 (s, 3 H), 1.56-1.50 (m, 2 H), 1.30-1.24 (m, 2 H); ESI-MS: m/z 422.4 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was quenched with water
  4. concentrationwas then concentrated to dryness in vacuo
  5. customThe crude product was purified by preparatory HPLC (35-55% MeCN/H2O gradient+0.01% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-1c8706c46a194e83924b676159e99c3f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461163B2

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