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Triethylamine → (S)-2-cyclopropyl-N-(1-(dimethylamino)-1-oxopropan-2-yl)-5-((2-(trimethyl-silyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 446950
ノート
印刷プレビュー

反応式

HRID 446950 の反応式
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([NH:15][C@@H:16]([CH3:20])[C:17](O)=[O:18])=[O:14])=[CH:11][N:10]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[CH2:29]([N:31](CC)[CH2:32]C)C.Cl.CNC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([NH:15][C@@H:16]([CH3:20])[C:17]([N:31]([CH3:32])[CH3:29])=[O:18])=[O:14])=[CH:11][N:10]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[C:7]3=[N:8][CH:9]=2)[CH2:2][CH2:3]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 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2724699PyBOPHCID 67387896(S)-2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoic acid

生成物 1

HCID 67388122(S)-2-cyclopropyl-N-(1-(dimethylamino)-1-oxopropan-2-yl)-5-((2-(trimethyl-silyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide
収率 70%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (S)-2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoic acid (253 mg, 0.63 mmol), triethylamine (0.44 mL, 3.13 mmol), and dimethylamine hydrochloride (102 mg, 1.25 mmol) in DMF (5 mL) at room temperature was added PyBOP (358 mg, 0.69 mmol). The reaction mixture was stirred overnight then diluted with EtOAc (50 mL) and washed with water (4×25 mL). The organic extracts were combined and dried (Na2SO4) then evaporated under vacuum. The crude residue was purified by SiO2 chromatography (24 g, hexanes:EtOAc, 3:7) to give 190 mg (70%) of (S)-2-cyclopropyl-N-(1-(dimethylamino)-1-oxopropan-2-yl)-5-((2-(trimethyl-silyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a colorless viscous oil.

後処理

  1. washwashed with water (4×25 mL)
  2. dry with materialdried (Na2SO4)
  3. customthen evaporated under vacuum
  4. customThe crude residue was purified by SiO2 chromatography (24 g, hexanes:EtOAc, 3:7)

出典と根拠

ORDレコード
ord-28cf7713142e445ab3499359a3504dee
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481541B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート