4-Aminotetrahydropyran hydrochloride → HCID 86693302, Verbindung

HRID 575273

Reaktionsgleichung

Reaktionsgleichung von HRID 575273
BrC1C=CC2OCCN3C(I)=C(C(N)=O)N=C3C=2C=1.Cl.NC1CCOCC1.Br[C:29]1[CH:30]=[CH:31][C:32]2[O:38][CH2:37][CH2:36][N:35]3[C:39]([C:45]([NH:47][CH:48]4[CH2:53][CH2:52][O:51][CH2:50][CH2:49]4)=[O:46])=[C:40]([C:42]([NH2:44])=[O:43])[N:41]=[C:34]3[C:33]=2[CH:54]=1.[CH3:55][C:56]1[O:60][N:59]=[C:58]([C@:61]([OH:65])([C:63]#[CH:64])[CH3:62])[CH:57]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CS(C)=O>[OH:65][C@:61]([C:58]1[CH:57]=[C:56]([CH3:55])[O:60][N:59]=1)([CH3:62])[C:63]#[C:64][C:29]1[CH:30]=[CH:31][C:32]2[O:38][CH2:37][CH2:36][N:35]3[C:39]([C:45]([NH:47][CH:48]4[CH2:53][CH2:52][O:51][CH2:50][CH2:49]4)=[O:46])=[C:40]([C:42]([NH2:44])=[O:43])[N:41]=[C:34]3[C:33]=2[CH:54]=1

Komponenten

7

Edukt 4

HCID 441186934-Aminotetrahydropyran hydrochlorideHCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 8669319110-Bromo-3-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 8669330310-bromo-N3-tetrahydropyran-4-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide

Produkt 1

HCID 86693302HCID 86693302, VerbindungAusbeute 6,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Similar to as described in Example 10 (carbonylative amidation) a mixture of 10-bromo-3-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide (200 mg, 0.46 mmol, 1.00 equiv), 4-aminotetrahydropyran hydrochloride (126 mg, 0.92 mmol, 2.00 equiv), Pd(dppf)Cl2 (34 mg, 0.05 mmol, 0.10 equiv), TEA (202 mg, 2.00 mmol, 4.00 equiv), and DMSO (5 mL) was stirred at 40° C. under an atmosphere of CO(g) overnight. The reaction was quenched with water and the solids were collected. This resulted in 250 mg (crude) of 10-bromo-N3-(tetrahydro-2H-pyran-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide as a brown solid. Similar to as described General Procedure F, 10-bromo-N3-(tetrahydro-2H-pyran-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide was reacted with (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol to give the titled compound as an off-white solid (38.6 mg, 6.6%).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. customthe solids were collected
  3. customThis resulted in 250 mg (crude) of 10-bromo-N3-(tetrahydro-2H-pyran-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide as a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-6d187100ecb94062b707d7a93c740fa9
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034866B2

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