Triethylamine → Pyrimidine-5-carboxylic acid-{1-[4-(4-chloro-2-fluoro-phenoxy)-3-fluoro-benzylcarbamoyl]-cyclopropyl}-amide hydrochloride

HRID 1406331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1406331
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([O:35][C:36]2[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][C:37]=2[F:44])=[C:33]([F:47])[CH:32]=1.[N:48]1[CH:53]=[C:52]([C:54]([NH:56][C:57]2([C:60](O)=[O:61])[CH2:59][CH2:58]2)=[O:55])[CH:51]=[N:50][CH:49]=1>O1CCCC1>[ClH:30].[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([O:35][C:36]2[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:60]([C:57]3([NH:56][C:54]([C:52]4[CH:51]=[N:50][CH:49]=[N:48][CH:53]=4)=[O:55])[CH2:59][CH2:58]3)=[O:61])=[CH:38][C:37]=2[F:44])=[C:33]([F:47])[CH:32]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584879074-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzylamineHCID 594962911-[(Pyrimidine-5-carbonyl)-amino]cyclopropanecarboxylic acid

Produkt 1

HCID 67447386Pyrimidine-5-carboxylic acid-{1-[4-(4-chloro-2-fluoro-phenoxy)-3-fluoro-benzylcarbamoyl]-cyclopropyl}-amide hydrochlorideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.5 mL (3.6 mmol) of triethylamine, 0.433 g (1.35 mmol) of TBTU and 325.5 mg (1.2 mmol) of 4-(4-chloro-2-fluoro-phenoxy)-3-fluoro-benzylamine were added to a solution of 250 mg (1.2 mmol) of 1-[(pyrimidine-5-carbonyl)-amino]-cyclopropanecarboxylic acid (from 1b) in 15 mL tetrahydrofuran and the mixture was stirred overnight at ambient temperature. Then the mixture was evaporated to dryness and the crude product thus obtained was purified by chromatography. The purified product was dissolved in approx. 4 mL ethyl acetate and the dropwise addition of ethereal hydrochloric acid solution caused the hydrochloride to precipitate out, which was then filtered off and dried.

Aufarbeitung

  1. customThen the mixture was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-dc8f9206c31b4873a9152464f0952e6f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916589B2

Notizen zur Reaktion

Wird geladen…