5-Nitro-2-Furoic Acid → HCID 53241492, compound

HRID 1941868Notes

Reaction equation

HRID 1941868 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[N+:19]([C:22]1[O:26][C:25]([C:27](O)=[O:28])=[CH:24][CH:23]=1)([O-:21])=[O:20]>>[NH2:16][C:10]1[O:11][CH2:12][C:13]([F:14])([F:15])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:27]([C:25]3[O:26][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=3)=[O:28])[CH:3]=[CH:4][C:5]=2[F:18])([CH3:17])[N:9]=1

Participants

3

Reactant 2

HCID 125775-Nitro-2-Furoic AcidHCID 58304207(R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

Product 1

HCID 53241492HCID 53241492, compound

Procedure

The condensation of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate XI-1) and 5-nitro-furan-2-carboxylic acid (CAS645-12-5) following procedure I yielded the title compound after purification by preparative HPLC. MS (ISP): m/z=399.3 [M+H]+.

Sources & evidence

ORD record
ord-3f8952eb5e6f4b0f883da3ebd34fed80
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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