Diisopropylethylamine → 3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-3-fluoro-pyridin-2-ylamino}-N-methoxy-4-methyl-benzamide

HRID 852027Notes

Reaction equation

HRID 852027 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].[CH3:24][NH:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(N(C(C)C)CC)(C)C.[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[N:25]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:24])#[N:23]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 12910381(2,2-Dimethylpropyl)(methyl)amineHCID 865888003-(6-chloro-5-cyano-3-fluoro-pyridin-2-ylamino)-N-methoxy-4-methyl-benzamide

Product 1

HCID 101790433-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-3-fluoro-pyridin-2-ylamino}-N-methoxy-4-methyl-benzamideYield 5.9%

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 (55.6 mg, 0.166 mmol), N-methyl-neopentylamine (70 mg, 0.511 mmol), diisopropylethylamine (0.1 mL) and potassium fluoride (12 mg) in DMSO (1 mL) was heated to 150° C. overnight. The product (3.9 mg, 5.9%) was isolated after purification by HPLC. C21H26FN5O2 MS m/e=400 (M+H).

Sources & evidence

ORD record
ord-dec5a37c56a048ab9e60437eba7d2512
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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