Triethylamine → HCID 69054539、化合物

HRID 730437ノート

反応式

HRID 730437 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:9]2[C:13]3=[N:14][C:15]([CH3:19])=[CH:16][C:17]([CH3:18])=[C:12]3[C:11]([C:20]#[N:21])=[C:10]2/[CH:22]=[CH:23]/[C:24](O)=[O:25])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.[O:41]1[CH2:46][CH2:45][CH:44]([NH2:47])[CH2:43][CH2:42]1.C(N(CC)CC)C>C1COCC1.O.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:9]2[C:13]3=[N:14][C:15]([CH3:19])=[CH:16][C:17]([CH3:18])=[C:12]3[C:11]([C:20]#[N:21])=[C:10]2/[CH:22]=[CH:23]/[C:24]([NH:47][CH:44]2[CH2:45][CH2:46][O:41][CH2:42][CH2:43]2)=[O:25])=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 441186934-Aminotetrahydropyran hydrochlorideHCID 69055515HCID 69055515、化合物

生成物 1

HCID 69054539HCID 69054539、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (250 mg, 0.570 mmol) in THF (2.5 ml) were added DMF (0.025 ml) and oxalylchloride (0.060 ml, 0.680 mmol), the mixture was stirred at room temperature for 1 hour and the solvent distilled off under reduced pressure. The residue was added under ice-cooling to a solution of tetrahydro-2H-pyran-4-ylamine hydrochloride (136 mg, 1.13 mmol), triethylamine (0.472 ml, 3.39 mmol) and THF (3 ml), and the mixture was stirred under ice-cooling for 2 hours and at room temperature for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the objective product as a solid material. The resultant material was recrystallized from hexane and ethyl acetate. Yield (amount) 200 mg, yield (rate) 66.7%

後処理

  1. distillationthe solvent distilled off under reduced pressure
  2. additionThe residue was added under ice-
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 2 hours and at room temperature for 12 hours
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-b57fecf71b754964ad887ba88ea4f5b2
出典データセット
uspto-grants-2009_09
特許番号
US07582651B2

反応ノート

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