Diisopropylethylamine → 4-(5-Cyano-[1,3,4]thiadiazol-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1426375ノート

反応式

HRID 1426375 の反応式
Cl[C:2]1[S:6][C:5]([C:7]#[N:8])=[N:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(C(C)C)CC)(C)C>C(#N)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:2]2[S:6][C:5]([C:7]#[N:8])=[N:4][N:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 112865425-Chloro-1,3,4-thiadiazole-2-carbonitrile

生成物 1

HCID 593235714-(5-Cyano-[1,3,4]thiadiazol-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester収率 91.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 5-chloro-[1,3,4]thiadiazole-2-carbonitrile (0.5 g, 3.44 mmol) (prepared by a procedure similar to that described in U.S. Pat. No. 5,736,545), and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.69 g, 3.44 mmol) and diisopropylethylamine (0.72 ml, 4.13 mmol) in acetonitrile (10 ml) was stirred at 130° C. for 30 min., under microwave irradiation. After this period, the solvent was evaporated in vacuo. The crude product was dissolved in dichloromethane and extracted with a saturated solution of ammonium chloride. The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by short open column chromatography (silica gel; 3-5% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo to yield D5 (0.97 g, 63%) as a white solid. C13H19N5O2S requires 309. Found 308 (MH+).

後処理

  1. customprepared by a procedure similar to
  2. waitAfter this period
  3. customthe solvent was evaporated in vacuo
  4. dissolutionThe crude product was dissolved in dichloromethane
  5. extractionextracted with a saturated solution of ammonium chloride
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customthe solvent evaporated in vacuo
  9. customThe crude product was purified by short open column chromatography (silica gel; 3-5% ammonia in methanol (7M)/dichloromethane)
  10. customThe desired fractions were collected
  11. customevaporated in vacuo

出典と根拠

ORDレコード
ord-43be422c1a0545a3ba6b67a9ec72c1ad
出典データセット
uspto-grants-2015_01
特許番号
US08933101B2

反応ノート

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