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1-Hydroxybenzotriazole → US9834551, Example 13

HRID 1500826
ノート
印刷プレビュー

反応式

HRID 1500826 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=3)[NH2:14])[CH:9]=2)[NH:4][CH:3]=1.[C:18](O)(=[O:23])/[CH:19]=[CH:20]/[CH2:21][CH3:22].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([NH:14][C:18](=[O:23])/[CH:19]=[CH:20]/[CH2:21][CH3:22])[CH:15]=[CH:16][CH:17]=3)[CH:9]=2)[NH:4][CH:3]=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 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 638122trans-2-Pentenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1176525073-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline

生成物 1

HCID 86301294US9834551, Example 13
収率 11.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 24 (50 mg, 0.2242 mmol) and trans-2-pentenoic acid 25 (24.6 mg, 0.246 eq) in DMF was added EDC.HCl (33 mg, 0.2706 mmol) and HOBt (36.5 mg, 0.2706 mmol). DIPEA (57.9 mg, 0.448 eq) was added to the reaction, stirred 12 h at RT and check the TLC for completion of the reaction and quench the reaction mixture with dilute water. The organic layer was treated with ethyl acetate (25 mL) and was washed with brine solution (25 mL) and dried over sodium sulphate, filtered and concentrated to get the crude product. The resulting oil was purified through silica gel chromatography using a gradient of 4% Ethyl acetate:hexane to afford 8 mg of Compound 26. MS-ES+305.1 1H NMR (400 MHz, DMSO-D6-d6): 11.45 (s, 1H), 10.08 (s, 1H), 8.40 (s, 1H), 8.17 (s, 1H), 7.85 (d, 1H), 7.61 (m, 1H), 7.36 (m, 2H), 7.30 (d, 1H), 5.62 (m, 1H), 2.35 (s, 3H).

後処理

  1. customfor completion of the reaction
  2. customquench the reaction mixture with dilute water
  3. additionThe organic layer was treated with ethyl acetate (25 mL)
  4. washwas washed with brine solution (25 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto get the crude product
  9. customThe resulting oil was purified through silica gel chromatography

出典と根拠

ORDレコード
ord-3484f4796ae34771a2c955d8b54d2c90
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206188B2

反応ノート

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