Tert-butyl (6'-{[(5-chloropyridin-2-yl)carbonyl]amino}-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)carbamate → N-(2-amino-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-6'-yl)-5-chloro pyridine-2-carboxamide

HRID 594893Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:33](=[CH:34][CH:35]=2)[O:32][C:31]([CH3:37])([CH3:36])[C:27]2([CH2:30][O:29][CH2:28]2)[C:14]23[CH2:18][O:17][C:16]([NH:19]C(=O)OC(C)(C)C)=[N:15]2)=[O:9])=[N:6][CH:7]=1>C1(C)C=CC=CC=1>[NH2:19][C:16]1[O:17][CH2:18][C:14]2([N:15]=1)[C:27]1([CH2:28][O:29][CH2:30]1)[C:31]([CH3:36])([CH3:37])[O:32][C:33]1[C:13]2=[CH:12][C:11]([NH:10][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:9])=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl (6′-{[(5-chloropyridin-2-yl)carbonyl]amino}-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl)carbamate (217 mg, 0.410 mmol), silica gel (neutral; 651 mg), and toluene (4 mL) was stirred for 80 minutes at 120° C. The reaction mixture was cooled down to ambient temperature and concentrated at reduced pressure. Purification of the residue with column chromatography on silica gel (eluted with EtOH/CHCl3=0/100 to 20/80) afforded N-(2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl)-5-chloropyridine-2-carboxamide (144 mg).

Workup

temperatureThe reaction mixture was cooled down to ambient temperature
concentrationconcentrated at reduced pressure
customPurification of the residue with column chromatography on silica gel (eluted with EtOH/CHCl3=0/100 to 20/80)

Sources & evidence

ORD record: ord-ac9db63457a3429ea85a25861c01063d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242973B2

Reaction notes

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