Acetic Acid → Formate

HRID 82092

Reaktionsgleichung

Reaktionsgleichung von HRID 82092
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[CH:6]([C:8]1[CH:9]=[C:10]([CH2:14][C:15]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[C:22]([C:24]([C:26]3[C:34]4[CH:33]=[N:32][CH:31]=[N:30][C:29]=4[N:28]([CH:35]([CH3:37])[CH3:36])[CH:27]=3)=[O:25])[CH:23]=2)=[O:16])[CH:11]=[CH:12][CH:13]=1)=O.[C:38]([OH:41])(=[O:40])C.[C:42]([O:45][BH-](OC(=O)C)OC(=O)C)(=[O:44])C.[Na+]>C(Cl)Cl.O>[CH:38]([OH:41])=[O:40].[N:2]1([CH2:6][C:8]2[CH:9]=[C:10]([CH2:14][C:15]([NH:17][C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]([C:26]4[C:34]5[CH:33]=[N:32][CH:31]=[N:30][C:29]=5[N:28]([CH:35]([CH3:37])[CH3:36])[CH:27]=4)=[O:25])[CH:23]=3)=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3]1.[CH:42]([O-:45])=[O:44]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochlorideHCID 866720722-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

Produkt 2

HCID 283FormateHCID 708172772-[3-(azetidin-1-ylmethyl)phenyl]-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide formate salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Azetidine hydrochloride (10 mg, 0.11 mmol) was added to a stirred solution of 2-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide (Preparation 192, 23 mg, 0.05 mmol) in DCM (1 mL) and acetic acid (0.04 mL, 0.60 mmol). The reaction mixture was stirred for 30 min at room temperature before addition of sodium triacetoxyborohydride (29 mg, 0.14 mmol) and stirring continued for 3 hours. Water (1 mL) was added and the mixture concentrated in vacuo (with toluene azeotroping). The residue was purified by preparative HPLC to afford the title compound as a formate salt in 12% yield, 3.4 mg.

Aufarbeitung

  1. concentrationthe mixture concentrated in vacuo (with toluene azeotroping)
  2. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d2d80c6da06f4393a1275495ee8ff960
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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