Ethyl chloroformate → Ethyl 3-(6-methyl-2-(1-(6-methylpyrimidin-4-yl)piperidin-4-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate

HRID 451487Notes

Reaction equation

HRID 451487 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[N:13]([N:18]=[C:19]([NH:21][CH:22]4[CH2:27][CH2:26][N:25]([C:28]5[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=5)[CH2:24][CH2:23]4)[N:20]=3)[CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:8]=[CH:9][CH:10]=1.C(N(CC)C(C)C)(C)C.Cl[C:45]([O:47][CH2:48][CH3:49])=[O:46]>ClCCl>[CH3:17][C:15]1[CH:16]=[C:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[CH2:4][NH:3][C:45](=[O:46])[O:47][CH2:48][CH3:49])[C:12]2[N:13]([N:18]=[C:19]([NH:21][CH:22]3[CH2:23][CH2:24][N:25]([C:28]4[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=4)[CH2:26][CH2:27]3)[N:20]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 67342484HCID 67342484, compound

Product 1

HCID 67344382Ethyl 3-(6-methyl-2-(1-(6-methylpyrimidin-4-yl)piperidin-4-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 8-(3-(aminomethyl)phenyl)-6-methyl-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine dihydrochloride (37 mg, 73.8 μmol) in dichloromethane (0.75 mL) was added N,N-diisopropylethylamine (38.1 mg, 51.5 μL, 295 mmol). To the resulting yellow solution was added ethyl chloroformate (8.99 mg, 7.89 μL, 81.2 mmol) and the reaction was stirred at room temperature over night. The title compound was obtained as a light yellow solid (35 mg, 95%) after column chromatography on silica gel using a gradient from methylene chloride to a mixture of methylene chloride/methanol 19:1 (v/v) as eluent. MS ISP (m/e): 501.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): (ppm)=8.51 (s, 1H), 8.13 (s, 1H), 7.83 (br s, 2H), 7.44 (t, 1H), 7.36 (s, 1H), 7.33 (d, 1H), 6.41 (s, 1H), 5.08 (br m, 1H), 4.53 (br d, 1H), 4.44 (d, 2H), 4.32 (br d, 2H), 4.15 (q, 2H), 3.96 (m, 1H), 3.69 (m, 1H), 3.20 (t, 2H), 3.10 (m, 1H), 2.40 (s, 3H), 2.38 (s, 3H), 2.22 (br d, 2H), 1.25 (t, 3H).

Sources & evidence

ORD record
ord-eae6533b9e7842a3bed86d1d47002113
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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