2,2-Difluoro-2-pyridin-2-ylethaneamine → HCID 178453010, compound

HRID 1171052Notes

Reaction equation

HRID 1171052 reaction equation
[C:1]([C:3]1[C:4]([CH2:11][C:12]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:23][N:22]=[C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:20]=3[CH:32]=2)=[O:13])=[N+:5]([O-:10])[C:6](Cl)=[CH:7][CH:8]=1)#[N:2].[F:33][C:34]([F:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[CH2:35][NH2:36]>CS(C)=O>[C:1]([C:3]1[C:4]([CH2:11][C:12]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:23][N:22]=[C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:20]=3[CH:32]=2)=[O:13])=[N+:5]([O-:10])[C:6]([NH:36][CH2:35][C:34]([F:43])([F:33])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 99641672,2-Difluoro-2-pyridin-2-ylethaneamineHCID 589729233-Cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-5-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide

Product 1

HCID 178453010HCID 178453010, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-5-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide (103 mg, 0.225 mmol) and 2,2-difluoro-2-pyridin-2-yl-ethylamine (89 mg, 0.534 mmol) (Organic Process Research & Development 8:192-200, 2004), in DMSO (3 mL) was stirred for 18 hrs at 80° C. LC/MS (ESI) (M+H+ 580.2) indicated the formation of desired product. After removing most DMSO by high-vacuum rotary evaporation, water was added, after which time precipitate formed. The liquid was loaded onto a 5 g FisherBrand PrepSep SPE C18 cartridge. The solid was washed with water a few times. The washes were also loaded onto the cartridge. The cartridge was then washed with water (40 mL), acetonitrile (20 mL), mixture of acetonitrile/DCM (1:1, 20 mL) and DMF (10 mL). All organic washes were combined and stripped off solvent by rotary evaporation. An orange solid was obtained and used without further purification. LC/MS (ESI): M+H+ 580.1.

Sources & evidence

ORD record
ord-9a800d44dcd54ce186d7b9a07426aea0
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

Loading…