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Triethylamine → 4-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 1645334
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1645334
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]([OH:13])=O)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][N:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C>ClCCl.CN(C=O)C>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([NH:39][C:11]([C:8]3[S:7][C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=4[CH:9]=3)=[O:13])=[CH:35][N:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 38545164-Chlorobenzo(b)thiophene-2-carboxylic AcidHCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

Produkt 1

HCID 462239524-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 4-chloro-benzo[b]thiophene-2-carboxylic acid (98 mg, 0.462 mmol), CH2Cl2 (5 mL), and a catalytic amount of DMF was stirred under Ar, and oxalyl chloride (2M in dichloromethane, 600 μL, 1.20 mmol) was dripped into the mixture over 5 min. The mixture was stirred at room temperature and after 1.0 hr the reaction was concentrated to dryness. Benzene was added and the solution was evaporated to dryness again. The white-yellow solid was re-dissolved in 5 mL of CH2Cl2 and dripped, under Ar, into a solution of 4-(5-amino-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (134 mg, 0.462 mmol), and triethylamine (102 μL, 1.0 mmol) in 5 mL of dichloromethane. The reaction was stirred at room temperature for 0.5 hr and then concentrated and the residue was taken up in 50 mL of EtOAc and washed with 50 mL of saturated ammonium chloride, brine and dried over anhydrous sodium sulfate. The EtOAc solvent was removed and the product was triturated with diethyl ether and hexanes (1:1 ratio), followed by filtration, to afford the product, 4-{5-[(4-chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester, as a pale green solid (80 mg, 38% yield). LCMS for C23H25ClN4O3S calcd. (m/e) 472, observed 471 (M−H).

Aufarbeitung

  1. concentrationwas concentrated to dryness
  2. additionBenzene was added
  3. customthe solution was evaporated to dryness again
  4. dissolutionThe white-yellow solid was re-dissolved in 5 mL of CH2Cl2
  5. stirringThe reaction was stirred at room temperature for 0.5 hr
  6. concentrationconcentrated
  7. washwashed with 50 mL of saturated ammonium chloride, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe EtOAc solvent was removed
  10. customthe product was triturated with diethyl ether and hexanes (1:1 ratio)
  11. filtrationfollowed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d481a77e877d46e2834c8f8346292458
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08124766B2

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