Diisopropylethylamine → 3-Bromo-4-methyl-N-(4-(2-(pyrrolidin-1-yl)ethyl)phenyl)benzamide

HRID 383874

Reaktionsgleichung

Reaktionsgleichung von HRID 383874
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([OH:16])=O.[N:21]1([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[Br:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([NH:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][CH2:26][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:29][CH:30]=1)=[O:16]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 821303-Bromo-4-methylbenzoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 64870474-(2-(Pyrrolidin-1-yl)ethyl)aniline

Produkt 1

HCID 684662633-Bromo-4-methyl-N-(4-(2-(pyrrolidin-1-yl)ethyl)phenyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

DIEA (473 μL, 2.72 mmol) was added into a solution of 3-bromo-4-methylbenzoic acid (189 mL, 0.881 mmol), 4-(2-(pyrrolidin-1-yl)ethyl)benzenamine (140 mg, 0.734 mmol), BOP (487 mg, 1.01 mmol) in DMF. The reaction mixture was stirred at rt under argon atmosphere overnight. The reaction mixture was diluted with AcOEt, and then washed with 1N NaOH aqueous solution three times. Organic phase was dried with anhydrous Na2SO4, and then evaporated to remove organic solvents. The obtained residue was further dried under high vacuum overnight to give crude product, which was used directly for the next step synthesis without further purification. MS (ESI+) m/z 387.0 [M+H]+.

Aufarbeitung

  1. washwashed with 1N NaOH aqueous solution three times
  2. dry with materialOrganic phase was dried with anhydrous Na2SO4
  3. customevaporated
  4. customto remove organic solvents
  5. customThe obtained residue was further dried under high vacuum overnight
  6. customto give crude product, which
  7. customwas used directly for the next step synthesis without further purification

Quellen und Nachweise

ORD-Eintrag
ord-94eccdfc318446c4999523b828f85fbe
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367686B2

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