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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 873746
Notes
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Reaction equation

HRID 873746 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 86724252Tert-butyl (6'-{[(5-chloropyridin-2-yl)carbonyl]amino}-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)carbamate

Product 1

HCID 72548694N-(2-amino-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-6'-yl)-5-chloro pyridine-2-carboxamideYield 81.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

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

Sources & evidence

ORD record
ord-14d5d8b3df584e27b21f62ccb8ec3f73
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08975415B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes