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 451487ノート

反応式

HRID 451487 の反応式
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

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 67342484HCID 67342484、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

出典と根拠

ORDレコード
ord-eae6533b9e7842a3bed86d1d47002113
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

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