Triethylamine → (E)-[2-(3-{4-[1-(4-Chloro-phenylcarbamoyl)-2-(3-diethylamino-pyrrolidin-1-yl)-ethyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

HRID 220194ノート

反応式

HRID 220194 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2N(CC)CC)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[O:10])=[CH:4][CH:3]=1.[C:30]([O:34][C:35](=[O:48])[NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][C:44](=[O:47])[CH:45]=[CH2:46])([CH3:33])([CH3:32])[CH3:31].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:71]([N:73](CC)[CH2:74][CH3:75])[CH3:72].[NH4+].[Cl-]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:30]([O:34][C:35](=[O:48])[NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][C:44](=[O:47])/[CH:45]=[CH:46]/[C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9](=[O:10])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:19][N:20]2[CH2:24][CH2:23][CH:22]([N:73]([CH2:74][CH3:75])[CH2:71][CH3:72])[CH2:21]2)=[CH:6][CH:7]=1)([CH3:33])([CH3:31])[CH3:32]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 80271Tri-o-tolylphosphineHCID 20786195HCID 20786195、化合物HCID 672315242-(4-Bromo-phenyl)-N-(4-chloro-phenyl)-3-(diethylamino-pyrrolidin-1-yl)-propionamide

生成物 1

HCID 59238288(E)-[2-(3-{4-[1-(4-Chloro-phenylcarbamoyl)-2-(3-diethylamino-pyrrolidin-1-yl)-ethyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(4-bromo-phenyl)-N-(4-chloro-phenyl)-3-(diethylamino-pyrrolidin-1-yl)-propionamide (826 mg, 1.72 mmol), (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (452 mg, 1.72 mmol), Pd2(dba)3 (47.3 mg, 0.051 mmol), tri-o-tolylphosphine (62.8 mg, 0.017 mmol) and triethylamine (694 mg, 6.88 mmol) in DMF (10 mL) was stirred at 100 degrees Celsius under N2 for 4 hours. After cooling to room temperature, the mixture was poured into a saturated aqueous solution of NH4Cl, and extracted with EtOAc (80 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and used directly without further purification. MS: calc'd 660 (MH+), exp 660 (MH+).

後処理

  1. extractionextracted with EtOAc (80 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customused directly without further purification

出典と根拠

ORDレコード
ord-76f732d0837145c1899ce89c0dd660e2
出典データセット
uspto-grants-2012_06
特許番号
US08202866B2

反応ノート

読み込み中…