Triethylamine → 1-Piperidinecarboxylic acid, ethyl ester

HRID 388568

反応式

HRID 388568 の反応式
ClC1C(NC2C=CC=CC=2S(C(C)C)(=O)=O)=NC(NC2C=C3C(CN([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)C3=O)=CC=2OC(C)C)=NC=1.C(N(CC)CC)C.Cl[C:50]([O:52][CH2:53][CH3:54])=[O:51]>CN(C=O)C>[CH2:53]([O:52][C:50]([N:22]1[CH2:21][CH2:20][CH2:19][CH2:24][CH2:23]1)=[O:51])[CH3:54]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24816438HCID 24816438、化合物

生成物 1

HCID 213991-Piperidinecarboxylic acid, ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 6-{5-Chloro-4-[2-(propane-2-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-2-piperidin-4-yl-2,3-dihydro-isoindol-1-one (Example 1, 15 mg, 0.025 mmol) and triethylamine (37.5 uL, 0.25 mmol) in DMF (0.5 mL), is added ethyl chloroformate (5.4 mg, 0.05 mmol). The mixture is stirred at room temperature for 1 hour. The crude reaction mixture is purified by mass-trigger preparative RP LC-MS to afford the title compound 446-{5-chloro-4-[2-(propane-2-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-1-carboxylic acid ethyl ester (175) as a white solid. 1H NMR 400 MHz (DMSO-d6 with trace D2O) δ 8.55 (d, 1H), 8.32 (s, 1H), 8.14 (s, 1H), 7.82 (dd, 1H), 7.74 (t, 1H), 7.34 (t, 1H), 7.28 (s, 1H), 4.73 (m, 2H), 4.39 (s, 2H), 4.12 (m, 2H), 4.06 (q, 2H), 3.46 (m, 1H), 2.92 (m 2H), 1.76 (m, 2H), 1.68 (m, 2H), 1.29 (d, 6H), 1.20 (t, 3H), 1.17 (d, 6H); MS m/z 671 (M+1).

後処理

  1. customThe crude reaction mixture
  2. customis purified by mass-trigger preparative RP LC-MS

出典と根拠

ORDレコード
ord-7f2c3fac5fda466c9cfad08f2d382125
出典データセット
uspto-grants-2013_02
特許番号
US08377921B2

関連ノート

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