Water → 2-(4-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)piperazin-1-yl)acetic acid

HRID 1498410ノート

反応式

HRID 1498410 の反応式
Cl[C:2]1[N:23]=[CH:22][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]4[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=[CH:16][N:15]=4)[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.[N:24]1([CH2:30][C:31]([O:33]CC)=[O:32])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C.CN1CCCC1=O.O1CCCC1.O.O.[OH-].[Li+]>>[CH:19]([N:18]1[C:14]([C:12]2[N:13]=[C:6]3[C:5]4[CH:22]=[N:23][C:2]([N:27]5[CH2:28][CH2:29][N:24]([CH2:30][C:31]([OH:33])=[O:32])[CH2:25][CH2:26]5)=[CH:3][C:4]=4[O:10][CH2:9][CH2:8][N:7]3[CH:11]=2)=[N:15][CH:16]=[N:17]1)([CH3:21])[CH3:20]

参加物

8

反応物 7

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 168937Lithium hydroxide, monohydrateHCID 207112Ethyl piperazine-1-acetateHCID 582045209-chloro-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine

生成物 1

HCID 582050192-(4-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)piperazin-1-yl)acetic acid

実験手順

A solution of 9-chloro-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine 317 (80.0 mg, 0.242 mmol), ethyl 2-(piperazin-1-yl)acetate (0.275 g, 1.60 mmol) and Triethylamine (0.400 mL, 2.87 mmol) in N-Methylpyrrolidinone (4.36 mL, 45.2 mmol) was heated at 150° C. for 2 days. The reaction was filtered thru celite then rinsed with EtOAc. The filtrate was washed water, brine. The organic layer was dried Na2SO4, concentrated. To a solution of crude ethy ester intermediate in Tetrahydrofuran (3.00 mL, 37.0 mmol) and Water (3.00 mL, 166 mmol) was added Lithium hydroxide hydrate (0.0406 g, 0.967 mmol). The reaction was stirred at r.t. The reaction was quenched with water then wash EtOAc. The aqueous layer was concentrated to give 2-(4-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)piperazin-1-yl)acetic acid which was carried to next reaction. MS: (ESI+)=439.2

後処理

  1. filtrationThe reaction was filtered thru celite
  2. washthen rinsed with EtOAc
  3. washThe filtrate was washed water, brine
  4. concentrationconcentrated
  5. customThe reaction was quenched with water
  6. concentrationThe aqueous layer was concentrated

出典と根拠

ORDレコード
ord-9120ba71895944d8b1f4dcd0eea514f1
出典データセット
uspto-grants-2015_12
特許番号
US09198918B2

反応ノート

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