Potassium Cyanide → HCID 57602477, compound

HRID 1787910Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=2[C:25]2[O:26][C:27](=[O:35])[C:28]3[CH:34]=[CH:33][N:32]=[CH:31][C:29]=3[N:30]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-]#N.[K+].[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([NH2:46])=[N:44][CH:45]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:22])[CH3:23])[CH:18]=[CH:17][C:16]=2[C:25]([NH:30][C:29]2[CH:31]=[N:32][CH:33]=[CH:34][C:28]=2[C:27]([NH:46][C:43]2[CH:42]=[CH:41][C:40]([Cl:39])=[CH:45][N:44]=2)=[O:35])=[O:26])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-[2-(1-tert-butoxycarbonylpiperidin-4-yl-oxy)-4-tert-butylphenyl]-4H-pyrido[3,4-d][1,3]oxazin-4-one (100 mg, 0.21 mmol), KCN (100 mg), 5-chloro-2-aminopyridine (53 mg, 0.42 mmol), and dry DMF (2 mL) was heated at 70° C. for 4 h, then quenched with brine (25 mL). The mixture was extracted with 10% MQOH in EtOAc (2×20 mL), and the combined extracts were washed with brine (3×100 mL) then dried over MgSO4. After filtering, the filtrate was concentrated to an oil which was purified by chromatography using 60% EtOAc in hexanes to give 30 mg of an oil which crystallized.

Workup

customquenched with brine (25 mL)
extractionThe mixture was extracted with 10% MQOH in EtOAc (2×20 mL)
washthe combined extracts were washed with brine (3×100 mL)
dry with materialthen dried over MgSO4
filtrationAfter filtering
concentrationthe filtrate was concentrated to an oil which
customwas purified by chromatography

Sources & evidence

ORD record: ord-871b6393702f46e4bccf3ff3709423c2
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511066B2

Reaction notes

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