Ethyl isocyanate → Ethyl 1-(5-{2-[(ethylcarbamoyl)amino]-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-7-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

HRID 712362Notes

Reaction equation

HRID 712362 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][C:7]1[N:38]=[C:10]2[CH:11]=[C:12]([C:20]3[CH:21]=[N:22][C:23]([N:26]4[CH2:31][CH2:30][C:29]([CH3:37])([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]4)=[N:24][CH:25]=3)[CH:13]=[C:14]([N:15]3[CH:19]=[CH:18][CH:17]=[N:16]3)[N:9]2[N:8]=1>O1CCOCC1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:38]=[C:10]2[CH:11]=[C:12]([C:20]3[CH:25]=[N:24][C:23]([N:26]4[CH2:31][CH2:30][C:29]([CH3:37])([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]4)=[N:22][CH:21]=3)[CH:13]=[C:14]([N:15]3[CH:19]=[CH:18][CH:17]=[N:16]3)[N:9]2[N:8]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 66977174Ethyl 1-{5-[2-amino-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-7-yl]pyrimidin-2-yl}-4-methylpiperidine-4-carboxylate

Product 1

HCID 66977033Ethyl 1-(5-{2-[(ethylcarbamoyl)amino]-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-7-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl isocyanate (143 mg, 2.01 mmol) was added to solution of ethyl 1-{5-[2-amino-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-7-yl]pyrimidin-2-yl}-4-methylpiperidine-4-carboxylate (180 mg, 0.40 mmol) in 1,4-dioxane (15 mL) and stirred at 80° C. for 22 h. LCMS showed desired product formation. The resultant black reaction mixture was concentrated in vacuo to give a brown tarry solid which was triturated with EtOAc (10 mL) to give the desired product as a grey solid (88 mg, 42%) MS: 519.23 [M+H]+.

Sources & evidence

ORD record
ord-863f03a4c72d4d10a17243195c2f7ffa
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…