Cyclohexanemethylamine → 4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid

HRID 1922190

Reaktionsgleichung

Reaktionsgleichung von HRID 1922190
CS(C1OC2C=C(OC3C=CN=C(C(NC)=O)C=3)C=CC=2N=1)=[O:3].C1(CN)CCCCC1.[CH:32]1([CH2:38][NH:39][C:40]2[O:41][C:42]3[CH:48]=[C:47]([O:49][C:50]4[CH:55]=[CH:54][N:53]=[C:52]([C:56](NC)=[O:57])[CH:51]=4)[CH:46]=[CH:45][C:43]=3[N:44]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([CH2:38][NH:39][C:40]2[O:41][C:42]3[CH:48]=[C:47]([O:49][C:50]4[CH:55]=[CH:54][N:53]=[C:52]([C:56]([OH:3])=[O:57])[CH:51]=4)[CH:46]=[CH:45][C:43]=3[N:44]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Komponenten

4

Edukt 3

HCID 76688CyclohexanemethylamineHCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamideHCID 577255594-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

Produkt 1

HCID 577255144-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid

Versuchsvorschrift

In Scheme 5, 4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide is aminated with cyclohexylmethanamine. The resulting 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide is then hydrolyzed to form 4-[2-(cyclohexylmethyl-amino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid. 4-[2-(Cyclohexylmethyl-amino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid then reacts with benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate, tert-butyl carbazate, and triethyl amine to form 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide. 4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide then reacts with trimethyl orthoformate to form a compound of the embodiments.

Quellen und Nachweise

ORD-Eintrag
ord-5027318c6e8a48aba64e524fd2c64e5d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173689B2

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