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Water → 1-[(5-chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine

HRID 1773327
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773327
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17](Br)=[N:16][C:15]=4[N:14]([CH3:27])[C:12]3=[O:13])=[N:7][C:6]=2[CH:28]=1.[C:29]([O:33][C:34]([C@@H:36]1[CH2:41][CH2:40][CH2:39][N:38](N)[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].O.C[N:51](C)C=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17]([N:38]5[CH2:39][CH2:40][CH2:41][CH:36]([C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[C@@H:37]5[NH2:51])=[N:16][C:15]=4[N:14]([CH3:27])[C:12]3=[O:13])=[N:7][C:6]=2[CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 29939704(R)-3-tert-butoxycarbonyl-aminopiperidineHCID 1180349711-[(5-Chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

Produkt 1

HCID 118035502
1-[(5-chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine
Ausbeute 72,6 %

Versuchsvorschrift

By utilizing the well known method, 1-[(5-chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 3b (460 mg, 0.96 mmol) was dissolved in N,N-dimethylformamide (12 ml). (R)-3-tert-butoxycarbonyl-aminopiperidine (193 mg, 0.96 mmol) and potassium carbonate (200 mg, 1.44 mmol) were added to give a reaction mixture. The reaction mixture was reacted at 75° C. for 2 hours, and TLC was used to monitor the reaction progress. After the reaction was completed, the obtained reaction mixture was cooled to room temperature. The cooled reaction solution was poured into cool water, suction filtered, and the obtained solid was washed with water, dried to give 1-[(5-chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine 3c (417 mg, grey solid), yield: 72.6%.

Aufarbeitung

  1. customto give a reaction mixture
  2. customThe reaction mixture was reacted at 75° C. for 2 hours
  3. customthe obtained reaction mixture
  4. customThe cooled reaction solution
  5. additionwas poured
  6. filtrationfiltered
  7. washthe obtained solid was washed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-266a89cad0f94b9e8200360448b2b201
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255098B2

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