Acetic Acid → (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-((R)-3,4-dimethylpiperazin-1-yl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

HRID 879610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879610
[C:1]([O:5][C@@H:6]([C:11]1[C:32]([CH3:33])=[CH:31][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][NH:27][C@H:26]([CH3:30])[CH2:25]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[C:41](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C=O>CN(C=O)C>[C:1]([O:5][C@@H:6]([C:11]1[C:32]([CH3:33])=[CH:31][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][N:27]([CH3:41])[C@H:26]([CH3:30])[CH2:25]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86700423(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-((R)-3-methylpiperazin-1-yl)pyrimidin-4-yl)benzo[d]thiazol-6-yl)acetate

Produkt 1

HCID 86700424(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-((R)-3,4-dimethylpiperazin-1-yl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To crude (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-((R)-3-methylpiperazin-1-yl)pyrimidin-4-yl)benzo[d]thiazol-6-yl)acetate (45.8 mg, 0.079 mmol) and sodium triacetoxyborohydride (83.7 mg, 0.395 mmol) in DMF (1 mL) was added acetic acid (23.7 mg, 22.6 μL, 0.395 mmol). The reaction mixture was heated to 60° C., then 37% w/w aq. formaldehyde (9.48 mg, 23.5 μL, 0.316 mmol) was added dropwise over 1 min. The reaction mixture was heated at 60° C. for 2 h. Upon completion of the reaction, the reaction mixture was filtered through Celite (ethyl acetate eluent) and concentrated. Purification by flash column chromatography on silica gel using 100:5:1 EtOAc/MeOH/NH4OH (0 to 100%) in EtOAc provided the product. LCMS-ESI+ calc'd for C31H37ClN5O3S (M+H+): 594.2; Found: 593.7 (M+H+).

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 60° C. for 2 h
  2. customUpon completion of the reaction
  3. filtrationthe reaction mixture was filtered through Celite (ethyl acetate eluent)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel using 100:5:1 EtOAc/MeOH/NH4OH (0 to 100%) in EtOAc
  6. customprovided the product

Quellen und Nachweise

ORD-Eintrag
ord-859513dc684e4c57aaffd6e1f33b408d
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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