Acetic acid;iodosylbenzene → tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 339052ノート

反応式

HRID 339052 の反応式
[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[N:14][C:15]([NH:18][NH2:19])=[CH:16][CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1.[CH3:28][O:29][CH2:30][CH2:31][O:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[CH:38][C:39]([CH:43]=O)=[N:40]2)=[CH:35][CH:34]=1.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O>CCO>[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:17]=[CH:16][C:15]3[N:14]([C:43]([C:39]4[CH:38]=[CH:37][C:36]5[C:41](=[CH:42][C:33]([O:32][CH2:31][CH2:30][O:29][CH3:28])=[CH:34][CH:35]=5)[N:40]=4)=[N:19][N:18]=3)[CH:13]=2)[C:8]([F:9])([F:10])[F:11])[CH2:3]1

参加物

5

反応物 3

HCID 73357407Acetic acid;iodosylbenzeneHCID 86707435tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 867074817-(2-Methoxyethoxy)quinoline-2-carbaldehyde

生成物 1

HCID 86707539tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate収率 92.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (53 mg, 0.14 mmol), 7-(2-methoxyethoxy)quinoline-2-carbaldehyde (30 mg, 0.13 mmol) and EtOH (1.4 mL) was stirred at ambient temperature overnight. The solvent was removed under reduced pressure. The residue was dissolved in DCM (1.4 mL) and iodosobenzene diacetate (54 mg, 0.17 mmol) was added. The reaction mixture was stirred at ambient temperature overnight and then loaded to a silica gel column eluting with 1:2 to 3:1 EtOAc/hexanes to give tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (72 mg, 92%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (1.4 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. washeluting with 1:2 to 3:1 EtOAc/hexanes

出典と根拠

ORDレコード
ord-4db7f348cb9749128fca467ce4829f63
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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