Triethylamine → 1-[3-[(N-Benzyl pyrrolidin-3-yl)carbamoyl]phenylcarbamoyl]-5-methylthio-6-trifluoromethyl indoline

HRID 1740811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1740811
[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([C:16](=[O:27])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24](O)=[O:25])[CH:19]=1)[CH2:7][CH2:6]2.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:41][CH:42]1[CH2:46][CH2:45][N:44]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:43]1>ClCCl.C1COCC1.CN(C=O)C>[CH2:47]([N:44]1[CH2:45][CH2:46][CH:42]([NH:41][C:24]([C:20]2[CH:19]=[C:18]([NH:17][C:16]([N:8]3[C:9]4[C:5](=[CH:4][C:3]([S:2][CH3:1])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=4)[CH2:6][CH2:7]3)=[O:27])[CH:23]=[CH:22][CH:21]=2)=[O:25])[CH2:43]1)[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27566131-Benzyl-3-aminopyrrolidineHCID 180051075-Methylthio-6-trifluoromethyl-1-(3-carboxy Phenyl Carbamoyl)indoline

Produkt 1

HCID 218330711-[3-[(N-Benzyl pyrrolidin-3-yl)carbamoyl]phenylcarbamoyl]-5-methylthio-6-trifluoromethyl indolineAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The carboxylic acid from Example 12 (0.5 g, 1.25 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.3 ml, 3.4 mmol) and DMF (catalytic). The solution was stirred for 1 hour and evaporated to dryness. The residue in dry THF (3 ml) was added to a stirred solution of triethylamine (0.3ml, 4 mmol) and 3-amino-N-benzyl pyrrolidine (0.79 g, 4.5 mmol) in dry THF (10 ml). Following 3 hours at room temperature the solution was partitioned (H2O/EtOAc). Drying and removal of solvent followed by rexst (EtOAc/60°-80° C. petrol) afforded the title compound (0.62 g, 89%) as a white powder. M.pt. 174°-175° C.

Aufarbeitung

  1. customevaporated to dryness
  2. waitFollowing 3 hours at room temperature
  3. customthe solution was partitioned (H2O/EtOAc)
  4. customDrying
  5. customremoval of solvent
  6. customfollowed by rexst (EtOAc/60°-80° C. petrol)

Quellen und Nachweise

ORD-Eintrag
ord-4446ed561dc24c1f8e7af2e8d3fe5339
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972937

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