Methylamine → 7-Fluoro-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17398Notes

Reaction equation

HRID 17398 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.[CH:21]([N:24](CC)C(C)C)(C)C.CN>ClCCl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([NH:24][CH3:21])=[N:6]2

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 510399667-Fluoro-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.20 g, 0.70 mmol) was dissolved in dichloromethane (10 ml), then N,N-diisopropylethylamine (0.15 ml, 0.88 mmol), methylamine (2 M tetrahydrofuran solution, 0.50 ml, 1.00 mmol) were added. After stirring in a sealed tube at an external temperature of about 60° C. for 3 hours, this was diluted with dichloromethane.

Sources & evidence

ORD record
ord-195bb4694fea4365a8b20d9304ca50b5
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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