N-Iodosuccinimide → 4-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-3-iodo-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester

HRID 1913240노트

반응식

HRID 1913240 반응식
[I:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[C:23]([N:25]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:22]3[N:42]=[CH:43][CH:44]=[C:21]3[N:20]=2)[CH2:15][CH2:14]1)=[O:12]>C(#N)C>[CH3:9][O:10][C:11]([CH:13]1[CH2:14][CH2:15][CH:16]([C:19]2[CH:24]=[C:23]([N:25]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:33])[CH3:31])[N:22]3[N:42]=[CH:43][C:44]([I:1])=[C:21]3[N:20]=2)[CH2:17][CH2:18]1)=[O:12]

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 66896532HCID 66896532, 화합물

생성물 1

HCID 667384164-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-3-iodo-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester수율 82.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

N-Iodosuccinimide (811 mg, 3.6 mmol) was added into a solution of 4-{7-[bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester (Int-7e, 1.75 g, 3.27 mmol) in acetonitrile (25 mL). The resulting reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and purified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient) to yield the title compound (1.79 g, 82.8% yield) at clear oil. LC-MS: 703 [M+H].

후처리

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient)

출처 및 근거

ORD 기록
ord-8fac5f20b03443fe9ea9f937d085ef25
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609675B2

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