Hydrochloric Acid → prop-1-en-2-yl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-ylcarbamate

HRID 1711695ノート

反応式

HRID 1711695 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([NH2:20])[N:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:32]([O:34][C:35]([CH3:37])=[CH2:36])=[O:33].Cl>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([NH:20][C:32](=[O:33])[O:34][C:35]([CH3:37])=[CH2:36])[N:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 93846Isopropenyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 588517633-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amine

生成物 1

HCID 67253039prop-1-en-2-yl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-ylcarbamate収率 348%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-tert-butyl-2-quinolin-6-yl-2H-pyrazol-3-ylamine from Example B3 (1.00 g, 3.8 mmol) in THF (20 mL) was cooled to −78° C. and treated with lithium bis(trimethylsilyl)amide (1.0 M in THF, 7.5 mL, 7.5 mmol). The resultant mixture was stirred at −78° C. for 30 min. Isopropenyl chloroformate (0.45 mL, 0.41 mmol) was added and stirring was continued at −78° C. for 30 min. The reaction mixture was quenched at −78° C. with aq HCl (2 N, 4 mL, 8 mmol), was warmed to RT and partitioned between water (200 mL) and EtOAc (200 mL). The organic layer was separated, washed with brine, dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to provide prop-1-en-2-yl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-ylcarbamate (0.5 g, 38% yield). MS (ESI) m/z: 351.2 (M+H+).

後処理

  1. custompartitioned between water (200 mL) and EtOAc (200 mL)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-88e4e94533fc4913bac1380b237a3284
出典データセット
uspto-grants-2010_09
特許番号
US07790756B2

反応ノート

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