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 220194노트

반응식

HRID 220194 반응식
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]

참가 물질

8

반응물 5

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

생성물 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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-76f732d0837145c1899ce89c0dd660e2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202866B2

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