Methylamine → HCID 18452511, compound

HRID 1271061Notes

Reaction equation

HRID 1271061 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[C:5](F)=[CH:6][C:7]2[O:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[C:9](=[O:22])[C:8]=2[CH:23]=1>>[Cl:3][C:4]1[C:5]([NH:2][CH3:1])=[CH:6][C:7]2[O:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[C:9](=[O:22])[C:8]=2[CH:23]=1

Participants

3

Reactant 2

HCID 6329Methylamine2×HCID 18452510HCID 18452510, compound

Product 1

HCID 18452511HCID 18452511, compoundYield 81%

Procedure

Analogous to Ex. 3, methyl amine displacement was performed using 6-chloro-7-fluoro-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.21 g, 0.16 mmol) and methyl amine (0.3 ml, 2M solution in tetrahydrofuran) to give 0.134 mg (81%) of 6-chloro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one. RP-HPLC: 2.38 min; ES-MS (M+H)+=334; 1H-NMR (DMSO-d6) δ (ppm): 3.1 (s, 3), 5.73 (s, 2), 6.2 (d, 1), 7.38 (d, 1), 7.61 (d, 2), 8.2 (d, 2).

Sources & evidence

ORD record
ord-6f170db26689488482fde474873b461f
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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