2-Pyridinecarboxylicacid,5-(2,2,3,3-tetrafluoropropoxy)- → HCID 53240606, compound

HRID 1941814Notes

Reaction equation

HRID 1941814 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@:8]2([CH3:19])[C:13]([F:15])([F:14])[C:12]([CH3:17])([CH3:16])[O:11][C:10]([NH2:18])=[N:9]2)[CH:7]=1.[F:21][C:22]([F:37])([CH:34]([F:36])[F:35])[CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31](O)=[O:32])=[N:29][CH:30]=1>>[NH2:18][C:10]1[O:11][C:12]([CH3:16])([CH3:17])[C:13]([F:14])([F:15])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:31]([C:28]3[CH:27]=[CH:26][C:25]([O:24][CH2:23][C:22]([F:37])([F:21])[CH:34]([F:36])[F:35])=[CH:30][N:29]=3)=[O:32])[CH:3]=[CH:4][C:5]=2[F:20])([CH3:19])[N:9]=1

Participants

3

Reactant 2

HCID 574758552-Pyridinecarboxylicacid,5-(2,2,3,3-tetrafluoropropoxy)-HCID 58304251(R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

Product 1

HCID 53240606HCID 53240606, compound

Procedure

The condensation of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate XI-2) and 5-(2,2,3,3-tetrafluoro-propoxy)-pyridine-2-carboxylic acid following procedure I yielded the 5-(2,2,3,3-tetrafluoro-propoxy)-pyridine-2-carboxylic acid [3-((R)-2-amino-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide which, after treatment with hydrochloric acid in dioxane (4N), evaporation and trituration with diethylether, gave the title compound as an off-white solid. MS (ISP): m/z=523.3 [M+H]+.

Sources & evidence

ORD record
ord-1f82bc7fad9b448dba0252b55471111c
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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