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Acetic Acid → HCID 68517236, Verbindung

HRID 2241434
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2241434
[F:1][C:2]1[CH:3]=[C:4]([NH:34][C:35]([C:37]2[C:42](=[O:43])[N:41]([C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)[CH:40]=[CH:39][N:38]=2)=[O:36])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[N:16]=[C:17]([CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:10]=12.[CH:51](=O)[CH3:52].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:15]2[C:11]3=[N:12][CH:13]=[CH:14][C:9]([O:8][C:7]4[CH:6]=[CH:5][C:4]([NH:34][C:35]([C:37]5[C:42](=[O:43])[N:41]([C:44]6[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=6)[CH:40]=[CH:39][N:38]=5)=[O:36])=[CH:3][C:2]=4[F:1])=[C:10]3[C:17]([CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([CH2:51][CH3:52])[CH2:21][CH2:20]3)=[N:16]2)=[CH:31][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68515107N-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(piperidin-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

Produkt 1

HCID 68517236HCID 68517236, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(4-(1-(4-methoxybenzyl)-3-(piperidin-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide (17 mg, 0.025 mmol; prepared as in Example 152, Step B) was added to a small round bottom flask and dissolved in dry THF (1.5 mL). Acetaldehyde (5.56 mg, 0.126 mmol) and a drop of acetic acid (d 1.049) were added. The reaction mixture was stirred for 10 minutes under N2(g) at room temperature. NaBH(OAc)3 (53.5 mg, 0.252 mmol) was added and stirred at room temperature for 1 hour. The reaction mixture was partitioned between water and DCM and extracted with a second portion of DCM (10 mL). The combined organics were dried over sodium sulfate and evaporated to afford desired product, used as crude in next step. Yield 18.6 mg, 90% purity by HPLC, 94%. LRMS (APCI pos) m/e 706.3 (M+H).

Aufarbeitung

  1. stirringstirred at room temperature for 1 hour
  2. customThe reaction mixture was partitioned between water and DCM
  3. extractionextracted with a second portion of DCM (10 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-30dc14130ca64821826a9f4a66d5996e
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723330B2

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