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Ammonium Chloride → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide

HRID 1962886
ノート
印刷プレビュー

反応式

HRID 1962886 の反応式
[NH2:1][C:2]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3]1.[CH3:8]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH4+].[Cl-].[C:32]([C:34]1[CH:35]=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][C:40]([O:44][C:45](C)([SH:49])[C:46](O)=[O:47])=[CH:39][CH:38]=2)#[CH:33]>CC#N.CCN(CC)CC>[C:32]([C:34]1[CH:35]=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][C:40]([O:44][CH:45]([S:49][CH3:8])[C:46]([NH:1][C:2]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3]1)=[O:47])=[CH:39][CH:38]=2)#[CH:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21624254(1-Aminocyclobutyl)methanolHCID 86647257(3-Ethynyl-quinolin-6-yloxy)-methyl sulfanyl-acetic acid

生成物 1

HCID 595653282-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒2 回

実験手順

To a mixture containing (1-amino-cyclobutyl)-methanol (preparation described in JP 08134044) (860 mg), aza-HOBT (600 mg), TBTU (1.41 g) and Et3N (1 ml) in CH3CN (30 ml), (3-ethynyl-quinolin-6-yloxy)-methyl sulfanyl-acetic acid dissolved in Et3N (1 ml) and CH3CN (30 ml) was added over 1 hr, at room temperature, under nitrogen atmosphere. The resulting brown suspension was stirred overnight at room temperature then poured into aq NH4Cl solution and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 1/3) to give 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide (1.09 g) as slightly yellow solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over sodium sulphate anhydrous
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 1/3)

出典と根拠

ORDレコード
ord-b5b2c18d0d9542fd91d48f0de30f6f26
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415272B2

反応ノート

読み込み中…

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