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Sodium triacetoxyborohydride → n-Cyclopropyl-2,4-difluoro-5-((2-phenyl-1h-pyrrolo[2,3-b]pyridin-5-yl)methylamino)benzamide

HRID 1684928
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1684928
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH:13][CH2:14][C:15]3[CH:16]=[C:17]4[CH:23]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[NH:21][C:18]4=[N:19][CH:20]=3)[CH:7]=2)[CH2:3][CH2:2]1.NC1C(F)=CC([F:44])=C(C=1)C(NC1CC1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(=O)C.ClCCl>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:7]=[C:8]([NH:13][CH2:14][C:15]3[CH:16]=[C:17]4[CH:23]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[NH:21][C:18]4=[N:19][CH:20]=3)[C:9]([F:12])=[CH:10][C:11]=2[F:44])[CH2:3][CH2:2]1
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Komponenten

6

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 219665075-amino-N-cyclopropyl-2,4-difluorobenzamideHCID 59190358n-Cyclopropyl-4-fluoro-3-{(2-phenyl-1h-pyrrolo[2,3-b]pyridin-5-yl)methylamino}benzamide

Produkt 1

HCID 24955944n-Cyclopropyl-2,4-difluoro-5-((2-phenyl-1h-pyrrolo[2,3-b]pyridin-5-yl)methylamino)benzamideAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of compound D of Example 1 (22 mg, 0.1 mmol), in a mixture of acetic acid and dichloromethane (1:1, 1 mL) were added 5-amino-N-cyclopropyl-2,4-difluorobenzamide (30 mg, 0.15 mmol) and NaBH(OAc)3 (30 mg, 0.2 mmol). The mixture was stirred at RT for 1 h. The reaction mixture was concentrated and the residue was purified by preparative RP HPLC. The appropriate fractions were collected and concentrated to remove methanol and saturated solution of NaHCO3 was added to precipitate out the desired product. The solid was filtered and dried in vacuo to give the title compound (6.5 mg) as a solid. LC/MS; (M+H)+=419.2

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative RP HPLC
  3. customThe appropriate fractions were collected
  4. concentrationconcentrated
  5. customto remove methanol and saturated solution of NaHCO3
  6. additionwas added
  7. customto precipitate out the desired product
  8. filtrationThe solid was filtered
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a9ce568bfd540ca991434a3c8a65bcb
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08148361B2

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