Tetrahydrofuran → (S)-4-(benzyloxycarbonylamino)-N-{1-[2-(trimethylsilyl)ethoxymethyl]pyrrolo[2,3-b]pyridin-4-yl}thiochromane-7-carboxamide

HRID 585743ノート

反応式

HRID 585743 の反応式
O1CCCC1.[NH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[CH:15][C:8]=12.C([Li])CCC.[CH2:29]([O:36][C:37]([NH:39][C@@H:40]1[C:49]2[C:44](=[CH:45][C:46]([C:50](Cl)=[O:51])=[CH:47][CH:48]=2)[S:43][CH2:42][CH2:41]1)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O>[CH2:29]([O:36][C:37]([NH:39][C@@H:40]1[C:49]2[C:44](=[CH:45][C:46]([C:50]([NH:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[CH:15][C:8]=34)=[O:51])=[CH:47][CH:48]=2)[S:43][CH2:42][CH2:41]1)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 223374571-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-amineHCID 87917945(S)-4-(benzyloxycarbonylamino)thiochromane-7-carboxylic acid chlorideHCID 178418339Butyllithium

生成物 1

HCID 69619656(S)-4-(benzyloxycarbonylamino)-N-{1-[2-(trimethylsilyl)ethoxymethyl]pyrrolo[2,3-b]pyridin-4-yl}thiochromane-7-carboxamide収率 42.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a tetrahydrofuran solution of 4-amino-1-[2-(trimethylsilyl)ethoxymethyl]pyrrolo[2,3-b]pyridine (1.32 g) was added dropwise n-butyllithium (1.59 M, 3.17 ml) and the mixture was stirred at the same temperature for 15 min. To this solution was added dropwise a tetrahydrofuran solution (20 ml) of (S)-4-(benzyloxycarbonylamino)thiochromane-7-carboxylic acid chloride (4.20 mmol) obtained by a similar reaction step as in Starting Material Synthetic Example 9 at 0° C. The reaction mixture was stirred at room temperature for 5 hr. Water (100 ml) was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and purified by silica gel column chromatography (hexane-ethyl acetate) to give the objective (S)-4-(benzyloxycarbonylamino)-N-{1-[2-(trimethylsilyl)ethoxymethyl]pyrrolo[2,3-b]pyridin-4-yl}thiochromane-7-carboxamide (1.06 g) as a pale-brown amorphous solid.

後処理

  1. customobtained by a similar reaction step as
  2. customat 0° C
  3. stirringThe reaction mixture was stirred at room temperature for 5 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe obtained organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. custompurified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-0847ac71695e469e9dbefe1780be4070
出典データセット
uspto-grants-2005_08
特許番号
US06933305B2

反応ノート

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