Ammonia → 2-[2-(Difluoromethyl)-4-methoxy-1h-benzimidazol-1-yl]-6-(4-morpholinyl)-9-(4-piperidinyl)-9h-purine

HRID 1256575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256575
[F:1][CH:2]([F:42])[C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[C:10]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[N:9]=2)[C:6]2[CH:36]=[CH:37][CH:38]=[C:39]([O:40][CH3:41])[C:5]=2[N:4]=1.C(O)(C(F)(F)F)=O.N>C(Cl)Cl>[F:42][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[C:10]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[N:9]=2)[C:6]2[CH:36]=[CH:37][CH:38]=[C:39]([O:40][CH3:41])[C:5]=2[N:4]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 67543947tert-butyl 4-[2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-9H-purin-9-yl]-1-piperidinecarboxylate

Produkt 1

HCID 666981762-[2-(Difluoromethyl)-4-methoxy-1h-benzimidazol-1-yl]-6-(4-morpholinyl)-9-(4-piperidinyl)-9h-purineAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Reaction of the above carbamate (165 mg, 0.282 mmol) with an excess of TFA (2 mL) in CH2Cl2 (10 mL) at room temperature for 1.5 hrs, followed by treatment with aq. NH3 gave 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-9-(4-piperidinyl)-9H-purine (121 mg, 88%), which was used in the next step without further purification: 1H NMR (CDCl3) δ 7.87 (s, 1H), 7.81 (dd, J=8.4, 0.5 Hz, 1H), 7.48 (t, J=53.6 Hz, 1H), 7.35 (t, J=8.2 Hz, 1H), 6.81 (d, J=7.8 Hz, 1H), 4.54 (tt, J=12.0, 4.1 Hz, 1H), 4.38 (br s, 4H), 4.07 (s, 3H), 3.88 (t, J=4.8 Hz, 4H), 3.30 (d, J=12.4 Hz, 2H), 2.86 (dt, J=12.4, 2.3 Hz, 2H), 2.20 (dd, J=11.8, 2.2 Hz, 2H), 2.04 (dq, J=12.3, 4.1 Hz, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-291f7d0769f4419db99baccb7539ed7f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461158B2

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