Acetic Acid → 2-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-3H-benzimidazol-5-carbonitrile

HRID 1851264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851264
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[NH:9][C:10]3[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:26]1([C:32]2[C:33]([C:41]3[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=3)=[N:34][C:35]3[N:36]([N:38]=[CH:39][CH:40]=3)[CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.ClCCl.CN(C=O)C>[C:26]1([C:32]2[C:33]([C:41]3[CH:42]=[CH:43][C:44]([CH2:45][N:2]4[CH2:3][CH2:4][CH:5]([C:8]5[NH:9][C:10]6[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:11]=6[N:12]=5)[CH2:6][CH2:7]4)=[CH:47][CH:48]=3)=[N:34][C:35]3[N:36]([N:38]=[CH:39][CH:40]=3)[CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

9

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 687529322-Piperidin-4-yl-1h-benzoimidazole-5-carbonitrile hydrochloride saltHCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Produkt 1

HCID 687516862-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-3H-benzimidazol-5-carbonitrileAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

265 mg (1 mmol) 2-piperidine-4-yl-3H-benzimidazole-5-carbonitrile hydrochloride salt was dissolved in 5 mL methanol. 204 mg (2 mmol) triethylamine, 250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde, 5 mL DMF, 12.5 mL dichloromethane and 131 mg (2.2 mmol) acetic acid were added and after 30 minutes stirring 355 mg (1.68 mmol) NaBH(OAc)3 was added. Additional NaBH(OAc)3 has been added after one, two, three and four hours (two equivalents each) and the reaction mixture has been stirred overnight at room temperature. Usual work-up and purification as described in previous experiments yields 138 mg of the desired material.

Aufarbeitung

  1. additionwas added
  2. customUsual work-up and purification

Quellen und Nachweise

ORD-Eintrag
ord-743b974d833e43ab8dfec5863ae02371
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957064B2

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