1-Methyl-3-aminopyrazole → HCID 25261181, compound

HRID 1966232Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1.[CH3:14][N:15]1[CH:19]=[CH:18][C:17]([NH2:20])=[N:16]1>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1N(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH:9]1([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:20][C:17]3[CH:18]=[CH:19][N:15]([CH3:14])[N:16]=3)=[N:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Bromo-5-cyclopentyloxy-pyridine (0.97 mmol), sodium-tert.-butylate (1.4 eq.), and 1-methyl-1H-pyrazole-3-amine (1.2 eq.) are dissolved in degassed dioxane (2 ml) and heated to 80° C. Chloro-(di-2-norbornylphosphino)(2-dimethylaminoferrocene-1-yl)palladium (II) (3 mg) in degassed dioxane (1 ml) is added and the reaction mixture is heated for 1 hour at 150° C. in the microwave. The reaction is quenched with ethylacetate/methanol (30 ml, 9:1) and filtrated over celite. The solvent of the filtrate is removed in vacuo. (5-Cyclopentyloxy-pyridine-2-yl)-(1-methyl-1H-pyrazole-3-yl)-amine (“A25”) is obtained after reversed phase column chromatography (water/acetonitrile+0.1% TEA) as a colorless powder in a yield of 29%; HPLC (method C): 1.55 min; LC-MS (method A): 0.97 min, 259.15 (M+H+);

Workup

temperaturethe reaction mixture is heated for 1 hour at 150° C. in the microwave
customThe reaction is quenched with ethylacetate/methanol (30 ml, 9:1)
filtrationfiltrated over celite
customThe solvent of the filtrate is removed in vacuo

Sources & evidence

ORD record: ord-d4f8b1c7e6424e87ae4d5eabe87c8c93
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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