1,2-Dichloroethane → (S)-tert-butyl 1-((5-(5-(benzylcarbamoyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate

HRID 2196514ノート

反応式

HRID 2196514 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]1[S:18][C:17]([N:19]2[C:23]([C:24](O)=[O:25])=[CH:22][C:21]([C:27]([F:30])([F:29])[F:28])=[N:20]2)=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:32]([NH:39][C:24]([C:23]1[N:19]([C:17]2[S:18][C:14]([CH2:13][NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:31])=[CH:15][CH:16]=2)[N:20]=[C:21]([C:27]([F:28])([F:30])[F:29])[CH:22]=1)=[O:25])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 69298544HCID 69298544、化合物

生成物 1

HCID 69095062(S)-tert-butyl 1-((5-(5-(benzylcarbamoyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate収率 45%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 25 (45 mg, 0.097 mmol) in CH2Cl2 (0.65 mL) were added benzylamine (0.016 mL, 0.146 mmol), EDC (37.3 mg, 0.195 mmol) followed by DMAP (4.76 mg, 0.039 mmol). The mixture was stirred for 16 h at room temperature. The mixture was quenched with a saturated sodium carbonate solution and extracted with ethyl acetate, washed with brine, dried (MgSO4) filtered and concentrated. The residue was purified by silica gel column chromatography with gradient of EtOAc (20-60%) in hexanes to afford 26a (24 mg, 45%) as a white solid. LRMS (ESI): calc. 551.2; found 574.6 (MNa)+.

後処理

  1. customThe mixture was quenched with a saturated sodium carbonate solution
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with gradient of EtOAc (20-60%) in hexanes

出典と根拠

ORDレコード
ord-74cb295bf6d84565bf638be08e298a5e
出典データセット
uspto-grants-2012_12
特許番号
US08338437B2

反応ノート

読み込み中…