Sodium triacetoxyborohydride → 5-{4-[4-(6-fluoro-1H-benzimidazol-2-yl)-piperidin-1-ylmethyl]-phenyl}-6-phenyl-pyrazolo[1,5-a]pyrimidine

HRID 1851270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851270
[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([N:13]=[CH:14][CH:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[F:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[C:32]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[NH:31][C:30]=2[CH:40]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[C:32]([CH:34]3[CH2:35][CH2:36][N:37]([CH2:20][C:19]4[CH:22]=[CH:23][C:16]([C:8]5[C:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)=[CH:12][N:11]6[N:13]=[CH:14][CH:15]=[C:10]6[N:9]=5)=[CH:17][CH:18]=4)[CH2:38][CH2:39]3)[NH:31][C:30]=2[CH:40]=1

Komponenten

4

Edukt 3

HCID 5049666Sodium triacetoxyborohydride2×HCID 534298905-Fluoro-2-piperidin-4-YL-1H-benzoimidazole hydrochloride2×HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Produkt 1

HCID 687537915-{4-[4-(6-fluoro-1H-benzimidazol-2-yl)-piperidin-1-ylmethyl]-phenyl}-6-phenyl-pyrazolo[1,5-a]pyrimidineAusbeute 59 %

Versuchsvorschrift

250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 258 mg (1 mmol) 6-fluoro-2-piperidine-4-yl-1H-benzimidazole hydrochloride salt were treated as previously described. Additional NaBH(OAc)3 has been added after one, two and three hours (two equivalents each). After a further hour stirring at room temperature additional 26 mg 6-fluoro-2-piperidine-4-yl-1H-benzimidazole hydrochloride salt and two equivalents NaBH(OAc)3 were added. After stirring overnight and two further additions of NaBH(OAc)3 the solvents were evaporated. Workup and purification yields 249 mg of the desired compound.

Aufarbeitung

  1. additionwere added
  2. customtwo further additions of NaBH(OAc)3 the solvents were evaporated
  3. customWorkup and purification

Quellen und Nachweise

ORD-Eintrag
ord-9f6ce07b32ad4e22b8207d12c5c608d0
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957064B2

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