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Formaldehyde → 3-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-7-(dimethylamino)-1,3-benzothiazol-6-yl}oxy)phenyl]benzamide

HRID 1097517
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1097517
N[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:37])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([C:35]#[N:36])([CH3:34])[CH3:33])[CH:27]=2)[CH:21]=[CH:22][CH:23]=1.[CH2:38]=O.[C:40]([BH3-])#[N:41].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[C:35]([C:32]([C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[C:25]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][C:3]2[CH:4]=[CH:5][C:6]3[N:7]=[C:8]([NH:11][C:12]([CH:14]4[CH2:16][CH2:15]4)=[O:13])[S:9][C:10]=3[C:2]=2[N:41]([CH3:40])[CH3:38])[CH:19]=1)=[O:37])([CH3:34])[CH3:33])#[N:36]
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Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59454488N-[3-({7-amino-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide

Produkt 1

HCID 594545003-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-7-(dimethylamino)-1,3-benzothiazol-6-yl}oxy)phenyl]benzamideAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-[3-({7-amino-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide (100 mg, 0.195 mmol) produced in Example 43 in acetic acid (2 mL) were added para-formaldehyde (36 mg, 1.19 mmol) and sodium cyanoborohydride (45 mg, 0.644 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (10 mL), washed successively with saturated aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80→80/20), and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (72 mg, 68%) as a white powder.

Aufarbeitung

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80→80/20)
  6. concentrationthe obtained solution was concentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-189d8f6cd27d4403ba9146ee76ef344a
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143258B2

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