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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2E)-3-(5-chloro-6-([(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino)-3-pyridinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide

HRID 226433
ノート
印刷プレビュー

反応式

HRID 226433 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:22]=[CH:23]/[C:24](O)=[O:25])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[CH2:10]1.[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][NH2:34].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:22]=[CH:23]/[C:24]([NH:34][O:33][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)=[O:25])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[CH2:10]1
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 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68962561(2E)-3-(5-chloro-6-{[(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylic acid

生成物 1

HCID 86603736(2E)-3-(5-chloro-6-([(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino)-3-pyridinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide
収率 77%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22728543Water ethylacetate溶媒

実験手順

A mixture of A mixture of (2E)-3-(5-chloro-6-{[(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylic acid (410 mg), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (142 mg), HOBt (156 mg) and EDCI (180 mg) in DMF (15 ml) was stirred at ambient temperature for 15 hours. The reaction mixture was poured into a mixture of AcOEt-H2O and the organic layer was washed with brine and dried over MgSO4. The solvent was evaporated in vacuo and the residue was chromatographed on silicagel eluting with AcOEt-MeOH (9:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give (2E)-3-(5-chloro-6-([(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino)-3-pyridinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (400 mg).

後処理

  1. washthe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was chromatographed on silicagel
  5. washeluting with AcOEt-MeOH (9:1)
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-e19a20e3808c4e9cb18bd849f215374e
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557127B2

反応ノート

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