5-Iodo-3-methylpyridin-2-amine → 3-(6-Aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one

HRID 1271057Notes

Reaction equation

HRID 1271057 reaction equation
[F:1][C:2]1[C:3]([NH:13][CH3:14])=[CH:4][C:5]2[O:10][CH2:9][NH:8][C:7](=[O:11])[C:6]=2[CH:12]=1.I[C:16]1[CH:17]=[C:18](C)[C:19]([NH2:22])=[N:20][CH:21]=1>>[NH2:22][C:19]1[N:20]=[CH:21][C:16]([N:8]2[C:7](=[O:11])[C:6]3[CH:12]=[C:2]([F:1])[C:3]([NH:13][CH3:14])=[CH:4][C:5]=3[O:10][CH2:9]2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 9595865-Iodo-3-methylpyridin-2-amineHCID 184525146-Fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one

Product 1

HCID 184524903-(6-Aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-oneYield 13.6%

Procedure

Analogous to the procedure described in Ex. 40, 6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.100 g, 0.51 mmol) and 5-iodo-3-methylpyridin-2-amine (0.119 g, 0.53 mmol) were coupled to yield pure 3-(6-aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.020 g, 13%) after reverse phase HPLC purification. ES-MS (M+H)+=303.

Sources & evidence

ORD record
ord-daf8a43b8e434e5a93d864b11e53b4fb
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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