Triethylamine → HCID 178501231, 화합물

HRID 75516노트

반응식

HRID 75516 반응식
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.[Cl:19][C:20]1[CH:21]=[N:22][C:23]([CH3:29])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:25]([C:24]2[C:23]([CH3:29])=[N:22][CH:21]=[C:20]([Cl:19])[CH:28]=2)=[O:26])[CH2:7][CH2:6]1)=[O:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 532566655-Chloro-2-methylnicotinoyl chloride2회HCID 178501207HCID 178501207, 화합물

생성물 1

HCID 178501231HCID 178501231, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Trans-4-Amino-cyclohexanecarboxylic acid methyl ester (2.14 g, 11.05 mmol) was suspended in THF (50 ml) and Et3N (2.79 g, 27.6 mmol) and cooled to 0° C. 5-Chloro-2-methylnicotinoyl chloride (Intermediate C) (2.20 g, 11.05 mmol) was slowly added portionwise and the reaction mixture was stirred at RT for 2 hours. The reaction mixture was partitioned between EtOAc and 1M HCl. The organic phase was washed with water, brine, dried over MgSO4, filtered and the solvent was removed in vacuo to afford the title product which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (1H, d), 7.42 (1H, 5), 7.80 (1H, d), 3.70 (1H, m), 3.60 (3H, s), 2.49 (3H, s), 2.29 (1H, m), 1.95 (4H, m), 1.42 (2H, m), 1.29 (2H, m); [M+H]+311.26.

후처리

  1. customThe reaction mixture was partitioned between EtOAc and 1M HCl
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-aa0407480a714ebbb9501ffac14f116e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835444B2

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