Dichloromethane → tert-Butyl 4-(6-methyl-2-(1-(6-methylpyrimidin-4-yl)piperidin-4-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 451482Notes

Reaction equation

HRID 451482 reaction equation
[NH2:1][C:2]1[N:24]=[C:5]2[C:6]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:7][C:8]([CH3:10])=[CH:9][N:4]2[N:3]=1.[CH3:25][C:26]1[N:31]=[CH:30][N:29]=[C:28]([N:32]2[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]2)[CH:27]=1.C(Cl)Cl>C(Cl)Cl.CO>[CH3:10][C:8]1[CH:7]=[C:6]([C:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH:12]=2)[C:5]2[N:4]([N:3]=[C:2]([NH:1][CH:35]3[CH2:36][CH2:37][N:32]([C:28]4[CH:27]=[C:26]([CH3:25])[N:31]=[CH:30][N:29]=4)[CH2:33][CH2:34]3)[N:24]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 61226887HCID 61226887, compoundHCID 673361314-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67342707tert-Butyl 4-(6-methyl-2-(1-(6-methylpyrimidin-4-yl)piperidin-4-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared in analogy to example 1h, starting from tert-butyl 4-(2-amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate and 1-(6-methylpyrimidin-4-yl)piperidin-4-one (see example 93b). The title compound was obtained as a light yellow solid (yield: 32%) after column chromatography on silica gel using a gradient from methylene chloride to methylene chloride/methanol 19:1 (v/v) as eluent.

Workup

  1. customPrepared in analogy to example 1h

Sources & evidence

ORD record
ord-0a8f50f21ec14fbbad1104422989a9a2
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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