Diisopropylethylamine → HCID 18445440, 화합물

HRID 460352

반응식

HRID 460352 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[C:8]1[NH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:7]=1[CH2:6]2.C([O:32][CH2:33][C:34](Cl)=[O:35])C1C=CC=CC=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:19][C:15]1[CH:14]=[C:13]([NH:12][C:11]2[C:7]3[CH2:6][C:5]4[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=4)[C:8]=3[N:9]([C:33](=[O:32])[CH2:34][OH:35])[N:10]=2)[CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 177085Benzyloxyacetyl chloride2회HCID 9797370Jnj-101984092회

생성물 1

HCID 18445440HCID 18445440, 화합물수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of (6,7-Dimethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine (Compound 14) (3.6 g, 10.0 mmol), Benzyloxy-acetyl chloride (Compound 27a) (2.2 g, 12.0 mmole) and DMF (50 mL) was added Diisopropylethylamine (5.2 mL, 30 mmole) at room temperature with stirring. The reaction was stirred at room temperature over night. The reaction was quenched with water and extracted with EtOAc. Dried over sodium sulfate and removed solvent in vacuo. The crude material was then taken up into ethanol and 0.5 g of Pd/C was added. The reaction was shaken on the hydrogenator over night. The reaction was filtered through Celite and removed solvent in vacuo. Triturated in a small amount of EtOAc. 3.2 g of ˜90% pure material was produced. 300 mg of the crude material was prepped on the Gilson and lyophilization gave Compound 432 as a white powder. MS m/z 384 (M+H)+;

후처리

  1. stirringThe reaction was stirred at room temperature over night
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialDried over sodium sulfate
  5. customremoved solvent in vacuo
  6. additionwas added
  7. stirringThe reaction was shaken on the hydrogenator over night
  8. filtrationThe reaction was filtered through Celite
  9. customremoved solvent in vacuo
  10. customTriturated in a small amount of EtOAc

출처 및 근거

ORD 기록
ord-149543929f314c7a99415f9992e517d4
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196110B2

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