Ammonia → (RS)-5-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid [3-(5-amino-3-cyclopropyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

HRID 1929506Notes

Reaction equation

HRID 1929506 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:33])=[C:21]([C:23]2([CH:30]3[CH2:32][CH2:31]3)[NH:28][C:27](=S)[CH2:26][O:25][CH2:24]2)[CH:22]=1.C(OO)(C)(C)C.[NH3:40]>>[NH2:40][C:27]1[CH2:26][O:25][CH2:24][C:23]([C:21]2[CH:22]=[C:17]([NH:16][C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:1])([F:15])[F:14])=[CH:10][N:9]=3)=[O:13])[CH:18]=[CH:19][C:20]=2[F:33])([CH:30]2[CH2:32][CH2:31]2)[N:28]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6410tert-Butyl hydroperoxideHCID 574758545-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acidHCID 58155241HCID 58155241, compound

Product 1

HCID 50992120(RS)-5-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid [3-(5-amino-3-cyclopropyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

Procedure

In an analogous manner to that described in example 6 (Method B), the condensation of 5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (CAS 881409-53-6) and (RS)-5-(5-amino-2-fluoro-phenyl)-5-cyclopropyl-morpholine-3-thione followed by the treatment with tert-butyl hydroperoxide and ammonia yielded the title compound (23) as a white solid. Mass (calculated) C21H20F4N4O3 [452.406]; (found) [M+H]+=453.

Sources & evidence

ORD record
ord-016cafec5bff4027896cfc6c56590ab7
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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