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Triethylamine → Methyl 4-amino-2-(2-methylmorpholino)thiazole-5-carboxylate

HRID 1958016
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HRID 1958016 반응식
[C:1]([N:3]=[C:4]([N:7]1[CH2:12][CH2:11][O:10][CH:9]([CH3:13])[CH2:8]1)[S:5][CH3:6])#[N:2].SC[C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C>CO>[NH2:2][C:1]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH3:13])[CH2:8]2)[S:5][C:6]=1[C:16]([O:18][CH3:19])=[O:17]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 80489835Methyl N-cyano-2-methylmorpholine-4-carbimidothioate

생성물 1

HCID 66780183Methyl 4-amino-2-(2-methylmorpholino)thiazole-5-carboxylate수율 93%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of methyl N-cyano-2-methylmorpholine-4-carbimidothioate (1.2 g, 6 mmol), methyl 2-mercaptoacetate (0.64 g, 6 mmol) and triethylamine (1.2 g, 12.0 mmol) in methanol (50 mL) was stirred at ambient temperature overnight. Solvent was removed. The residue was dissolved in dichloromethane, washed with water and brine. The organic layer was concentrated to give the desired product (crude, 1.4 g, 93%). 1H NMR (300 MHz, CDCl3) δ 5.81 (br, 2H), 3.97˜3.94 (m, 1H), 3.75 (s, 3H), 3.69-3.59 (m, 3H), 3.28-3.14 (m, 1H), 2.87-2.80 (m, 1H), 1.22 (d, J=6.0 Hz, 3H); LC-MS: 258 (MH+).

후처리

  1. customSolvent was removed
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water and brine
  4. concentrationThe organic layer was concentrated

출처 및 근거

ORD 기록
ord-2e5d5c23ab1b468680fa691727ec48ff
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410095B2

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