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Methylamine → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-{5-[(methylamino)methyl]-2-thienyl}-1H-indole-7-carboxamide

HRID 1806295
ノート
印刷プレビュー

反応式

HRID 1806295 の反応式
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[S:22][C:23]([CH:26]=O)=[CH:24][CH:25]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[CH3:31][NH2:32].C1COCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(O)(=O)C>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[S:22][C:23]([CH2:26][NH:32][CH3:31])=[CH:24][CH:25]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]
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 6329MethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 577326703-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-2-thienyl)-1H-indole-7-carboxamide

生成物 1

HCID 426290303-[1-(ethylsulfonyl)-4-piperidinyl]-5-{5-[(methylamino)methyl]-2-thienyl}-1H-indole-7-carboxamide収率 20%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-2-thienyl)-1H-indole-7-carboxamide (35 mg, 0.078 mmol) in DMSO (1.0 mL) was added acetic acid (3 drops), 2 M methylamine in THF (0.24 mL, 0.471 mmol), and reacted for 3 h. Sodium triacetoxyborohydride (100 mg, 0.471 mmol) was then added and reaction was stirred overnight. All solvent was removed in vacuo and purified by Gilson Preparatory HPLC. The impure desired fraction was concentrated under reduced pressure and loaded onto a 500 mg SCX SPE cartridge primed with 10 mL of methanol. The cartridge was then sequentially eluted with 2M NH3 in MeOH (10 mL×2). The NH3 in MeOH fractions were concentrated to give 7.3 mg of the title compound (20%).

後処理

  1. customreacted for 3 h
  2. customreaction
  3. customAll solvent was removed in vacuo
  4. custompurified by Gilson Preparatory HPLC
  5. concentrationThe impure desired fraction was concentrated under reduced pressure
  6. washThe cartridge was then sequentially eluted with 2M NH3 in MeOH (10 mL×2)
  7. concentrationThe NH3 in MeOH fractions were concentrated

出典と根拠

ORDレコード
ord-7a60fef6136141c4ae2b16813865a5d2
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354406B2

反応ノート

読み込み中…

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