Triethylamine → Methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate

HRID 72428

反応式

HRID 72428 の反応式
[ClH:1].[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.C(N(CC)CC)C.Cl[C:15]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=1>CO>[Cl:1][C:18]1[CH:17]=[N:16][C:15]([N:2]2[CH2:5][CH:4]([OH:6])[CH2:3]2)=[C:20]([CH:19]=1)[C:21]([O:23][CH3:24])=[O:22]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 819931Methyl 2-chloronicotinateHCID 27592903-Hydroxyazetidine hydrochloride

生成物 1

HCID 67958303Methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
150 °C

実験手順

To a solution of azetidin-3-ol hydrochloride (637 mg, 5.82 mmol, commercially available from Matrix Scientific #011272) and trietylamine (1.69 ml, 12.11 mmol) in methanol (10 ml), methyl 2-chloropyridine-3-carboxylate (1 g, 4.84 mmol) was added and the mixture stirred at 150° C. under microwave irradiation 10 min (2 cycles of 5 min each). The residue obtained after solvent evaporation was purified by SPE-Si cartridge (10 g) eluting with a mixture cyclohexane/ethylacetate from 90/10 to 60/40. Collected fractions after solvent evaporation afforded the title compound (D62) (D004/099/1) (800 mg)

後処理

  1. customThe residue obtained
  2. customafter solvent evaporation
  3. customwas purified by SPE-Si cartridge (10 g)
  4. washeluting with a mixture cyclohexane/ethylacetate from 90/10 to 60/40
  5. customCollected fractions after solvent evaporation

出典と根拠

ORDレコード
ord-a40d6ea9459f469596356e90bc537a2c
出典データセット
uspto-grants-2014_09
特許番号
US08828987B2

関連ノート

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