Diethyl Ether → HCID 57602450, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C(OCC)C.C([Mg]Br)C=C.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[C:37]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[CH:36]=[CH:35][C:34]=2[C:44]2[O:45][C:46](=[O:54])[C:47]3[CH:53]=[CH:52][N:51]=[CH:50][C:48]=3[N:49]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[C:37]([N:39]3[CH2:40][CH2:41][CH2:42][CH2:43]3)[CH:36]=[CH:35][C:34]=2[C:44]([NH:49][C:48]2[CH:50]=[N:51][CH:52]=[CH:53][C:47]=2[C:46]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=2)=[O:54])=[O:45])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]Participants
6
Procedure
A solution of 2-amino-5-chloropyridine (52 mg, 0.4 mmol) in THF (10 mL) was cooled to 0° C. and treated with a 1 M diethyl ether solution of allylmagnesium bromide (0.4 mL). The mixture was stirred for 5 minutes before adding 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)phenyl]-4H-pyrido[3,4-d][1,3]oxazin-4-one (100 mg, 0.2 mmol). The reaction mixture was stirred overnight at ambient temperature then concentrated to dryness under vacuum. The residue was treated with brine (5 mL) and CHCl3 (20 mL). The layers were separated and the organic layer was chromatographed using 1% MeOH in CHCl3 to give 125 mg (0.2 mmol, 99%) of product as a solid.
Workup
- stirringThe reaction mixture was stirred overnight at ambient temperature
- concentrationthen concentrated to dryness under vacuum
- additionThe residue was treated with brine (5 mL) and CHCl3 (20 mL)
- customThe layers were separated
- customthe organic layer was chromatographed
Sources & evidence
- ORD record
- ord-5575b543a6ca43cabe4e4beafdc4cd23
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07511066B2
Reaction notes
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