1,3-Propanediamine → HCID 10164511, Verbindung

HRID 1373838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373838
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26](F)[CH:25]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)[N:10]3[N:9]=2)=[CH:4][CH:3]=1.[NH2:31][CH2:32][CH2:33][CH2:34][NH2:35]>>[NH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:26]1[CH:25]=[C:24]([C:23]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][N:10]3[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:9][CH2:8][CH2:23][CH2:11][NH2:10])[CH:17]=4)=[CH:14][CH:13]=[CH:12][C:11]=23)[CH:29]=[CH:28][N:27]=1

Komponenten

3

Edukt 2

HCID 4281,3-PropanediamineHCID 10157930HCID 10157930, Verbindung

Produkt 1

HCID 10164511HCID 10164511, VerbindungAusbeute 46 %

Versuchsvorschrift

A solution of 2-(4-fluorophenyl)-3,7-bis(2-fluoropyridin-4-yl)pyrazolo[1,5-α]pyridine (34 mg, 0.08 mmol) in 1,3-diaminopropane (1 mL) was heated at 150° C. for 0.25 hours. Upon cooling to room temperature, the mixture was concentrated in vacuo and the residue was triturated with hot ethyl acetate. The resulting solids were collected on filter, washed with ethyl ether and dried to provide N-{4-[3-{2-[(3-aminopropyl)amino]pyridin-4-yl}-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-yl]pyridin-2-yl}propane-1,3-diamine as a light yellow powder (19 mg, 46%). 1H NMR (CD3OD): δ 8.18 (d, 1H), 8.03 (d, 1H), 7.78 (d, 1H), 7.65 (dd, 2H), 7.45 (dd, 1H), 7.30 (s, 1H), 7.1–7.2 (m, 4H), 6.60 (s, 1H), 6.59 (d, 1H), 3.55 (t, 2H), 3.47 (t, 2H), 3.0 (q, 4H), 1.88–2.04 (m, 4H); MS m/z 511 (M+1).

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was triturated with hot ethyl acetate
  3. customThe resulting solids were collected
  4. filtrationon filter
  5. washwashed with ethyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-20ecc05d187d4db890cf0dcba5183a6c
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163940B2

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