Triethylamine → HCID 178501231, 화합물

HRID 1914666노트

반응식

HRID 1914666 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 chlorideHCID 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) is suspended in THF (50 mL) and Et3N (2.79 g, 27.6 mmol) and cooled to 0° C. 5-chloro-2-methylnicotinoyl chloride (step 1) (2.20 g, 11.05 mmol) is slowly added portionwise and the RM is stirred at r.t. for 2 hours. LCMS showed mainly product. The reaction mixture is partitioned between EtOAc and 1M HCl. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent is removed in vacuo to afford the title product which is 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); [MH]+311.26.

후처리

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

출처 및 근거

ORD 기록
ord-cbf3c14e57204cbf899b2f85df8280c4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614213B2

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