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4-Methylthiophene-2-carbonyl chloride → 1-Methyl-2-{2-[(4-methyl-thiophene-2-carbonyl)-amino]-pyrimidin-4-yl}-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 1036601
ノート
印刷プレビュー

反応式

HRID 1036601 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:24])[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:27]1[CH:28]=[C:29]([C:32](Cl)=[O:33])[S:30][CH:31]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:24])[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:32]([C:29]4[S:30][CH:31]=[C:27]([CH3:26])[CH:28]=4)=[O:33])[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:25])=[O:7])([CH3:4])([CH3:3])[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

5

反応物 2

HCID 27955254-Methylthiophene-2-carbonyl chlorideHCID 247765532-(2-Amino-pyrimidin-4-yl)-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

生成物 1

HCID 672847501-Methyl-2-{2-[(4-methyl-thiophene-2-carbonyl)-amino]-pyrimidin-4-yl}-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester収率 96.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine
触媒
HCID 1049Pyridine溶媒

実験手順

2-(2-Amino-pyrimidin-4-yl)-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (prepared as described in Example 9) (300 mg, 0.873 mmol) was suspended in dry pyridine under nitrogen atmosphere and sonicated for 2 minutes. 4-Methyl-thiophene-2-carbonyl chloride (0.142 mL, 1.135 mmol, 1.3 eq) and DMAP (10 mg, 0.087 mmol, 0.1 eq) were added and the mixture was stirred at room temperature for 3 hours. Pyridine was then evaporated and the residue was taken up with saturated aqueous NaHCO3 (10 mL) and extracted with ethyl acetate (3×10 mL). Combined organic layers were washed with brine (3×10 mL), dried over Na2SO4 and evaporated to dryness. The crude product was purified by chromatography on silica gel (gradient n-hexane/ethyl acetate 1:1 to pure ethyl acetate) to obtain 394 mg of 1-methyl-2-{2-[(4-methyl-thiophene-2-carbonyl)-amino]-pyrimidin-4-yl}-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (85%).

後処理

  1. customsonicated for 2 minutes
  2. customPyridine was then evaporated
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. washCombined organic layers were washed with brine (3×10 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe crude product was purified by chromatography on silica gel (gradient n-hexane/ethyl acetate 1:1 to pure ethyl acetate)

出典と根拠

ORDレコード
ord-9360136ba5fa45719d9c1f20147dfc35
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546413B2

反応ノート

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