6-chloropyridazine-3-carboxylic Acid → HCID 53240708, compound

HRID 1941821Notes

Reaction equation

HRID 1941821 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.[Cl:21][C:22]1[N:27]=[N:26][C:25]([C:28](O)=[O:29])=[CH:24][CH:23]=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:28]([C:25]3[N:26]=[N:27][C:22]([Cl:21])=[CH:23][CH:24]=3)=[O:29])[CH:3]=[CH:4][C:5]=2[F:20])([CH3:19])[N:9]=1

Participants

3

Reactant 2

HCID 64157626-chloropyridazine-3-carboxylic AcidHCID 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 53240708HCID 53240708, 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 6-chloro-pyridazine-3-carboxylic acid following procedure I yielded the 6-chloro-pyridazine-3-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 a white solid. MS (ISP): m/z=428.2 [M+H]+.

Sources & evidence

ORD record
ord-9fbeecb580554944b3c349a6b24130e5
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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