Hydrochloric Acid → tert-Butyl 2-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

HRID 1261356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261356
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:15])[S:13][C:6]=12.[BH4-].[Na+].Cl>CO.C1COCC1.Cl[Ni]Cl>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:15])[S:13][C:6]=23)=[C:2]([F:1])[CH:30]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59424685tert-Butyl 2-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

Produkt 1

HCID 59424551tert-Butyl 2-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24385Nickel DichlorideKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 292 (80 mg, 0.17 mmol) in MeOH/THF (1.7 mL/1.7 mL) at 0° C., was added NiCl2×6H2O (85 mg, 0.35 mmol), followed by addition of NaBH4 (26 mg, 0.68 mmol), portion wise. The reaction mixture was stirred for 15 min, treated with 2N aqueous HCl (2 mL), filtered; the filtrate was neutralized with aqueous NH4OH to pH 7 and partitioned between EtOAc and water. Organic phase was collected, dried over anhydrous Na2SO4 and concentrated. The residue (75 mg, quantitative yield, crude) was used directly in next step without further purification. MS (m/z): 447.1(M+H) (found).

Aufarbeitung

  1. filtrationfiltered
  2. custompartitioned between EtOAc and water
  3. customOrganic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue (75 mg, quantitative yield, crude) was used directly in next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-1fda7b9ff4754b088869b62fc47964e2
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470850B2

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