Diisopropylethylamine → N-[5-(4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidine-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide

HRID 241094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241094
Cl.[O:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]3[S:17][C:16]([NH:18][C:19](=[O:21])[CH3:20])=[N:15][CH:14]=3)=[CH:12][C:7]=2[CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:23]1[C:28]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[C:27]([CH3:37])[N:26]=[CH:25][N:24]=1.C(N(C(C)C)CC)(C)C>CN1CCCC1>[F:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][C:28]2[C:23]([N:5]3[CH2:6][C:7]4[CH:12]=[C:11]([C:13]5[S:17][C:16]([NH:18][C:19](=[O:21])[CH3:20])=[N:15][CH:14]=5)[CH:10]=[CH:9][C:8]=4[O:2][CH2:3][CH2:4]3)=[N:24][CH:25]=[N:26][C:27]=2[CH3:37])=[CH:35][CH:34]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 86647837N-[5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide hydrochlorideHCID 866478404-Chloro-5-(4-fluorobenzyl)-6-methylpyrimidine

Produkt 1

HCID 86647839N-[5-(4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidine-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 84541-MethylpyrrolidineLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of N-[5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide hydrochloride (220 mg, 0.68 mmol), 4-chloro-5-[(4-fluorophenyl)methyl]-6-methylpyrimidine (reagent preparation 5) (152 mg, 0.64 mmol) and diisopropylethylamine (500 mg, 3.87 mmol) in N-methylpyrrolidine (4 mL) was heated in a microwave reactor at 120° C. for 3 h. The reaction mixture was concentrated, diluted with water (10 mL), the precipitate was filtered off, washed with water (2×5 mL) and methanol (5 mL), and dried to provide N-[5-(4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidine-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide (147 mg, 47% yield) as a off-white solid. MS (EI) C26H24FN5O2S: 490 (MH+).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (10 mL)
  3. filtrationthe precipitate was filtered off
  4. washwashed with water (2×5 mL) and methanol (5 mL)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3a08bd763f24490594d9d6be62e5eefb
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

Notizen zur Reaktion

Wird geladen…