Neopentylamine → 3-[5-Cyano-6-(2,2-dimethyl-propylamino)-3-fluoro-pyridin-2-ylamino]-N-methoxy-4-methyl-benzamide

HRID 1666068Notes

Reaction equation

HRID 1666068 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[CH3:20])[C:12]([NH:14][O:15][CH3:16])=[O:13])[C:5]([F:21])=[CH:4][C:3]=1[C:22]#[N:23].[CH2:24]([NH2:29])[C:25]([CH3:28])([CH3:27])[CH3:26].[F-].[K+]>CS(C)=O>[C:22]([C:3]1[CH:4]=[C:5]([F:21])[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[CH3:20])[C:12]([NH:14][O:15][CH3:16])=[O:13])=[N:7][C:2]=1[NH:29][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])#[N:23]

Participants

5

Reactant 3

HCID 79882NeopentylamineHCID 522689Potassium FluorideHCID 865888003-(6-chloro-5-cyano-3-fluoro-pyridin-2-ylamino)-N-methoxy-4-methyl-benzamide

Product 1

HCID 101781373-[5-Cyano-6-(2,2-dimethyl-propylamino)-3-fluoro-pyridin-2-ylamino]-N-methoxy-4-methyl-benzamideYield 1.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-(6-chloro-5-cyano-3-fluoro-pyridin-2-ylamino)-N-methoxy-4-methyl-benzamide (52 mg, 0.15 mmol), neopentylamine (0.12 mL) and potassium fluoride (12 mg) in DMSO (1 mL) was heated to 150° C. overnight. The product (1.1 mg, 1.8%) was isolated after purification by HPLC. C20H24FN5O2 MS m/e=386 (M+H).

Sources & evidence

ORD record
ord-6310500492ab4839aa862b546139f09a
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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