Triethylamine → HCID 178501231、化合物

HRID 2391028ノート

反応式

HRID 2391028 の反応式
[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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 532566655-Chloro-2-methylnicotinoyl chlorideHCID 178501207HCID 178501207、化合物

生成物 1

HCID 178501231HCID 178501231、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-26abc113f6944305880bee58f8b89c24
出典データセット
uspto-grants-2012_09
特許番号
US08273900B2

反応ノート

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