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Ethylenediamine → HCID 178481763, 화합물

HRID 246787
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HRID 246787 반응식
[OH:1][C@H:2]1[CH2:5][C@H:4]([NH:6][C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[C:26]5[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=5)[N:20]([CH3:28])[N:19]=4)[N:16]=3)[N:11](COCC[Si](C)(C)C)[CH:10]=2)=[O:8])[CH2:3]1.FC(F)(F)C(O)=O.C(N)CN>ClCCl.O.C(OCC)(=O)C>[OH:1][C@H:2]1[CH2:3][C@H:4]([NH:6][C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[C:26]5[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=5)[N:20]([CH3:28])[N:19]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:8])[CH2:5]1
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참가 물질

7

반응물 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 178481751HCID 178481751, 화합물

생성물 1

HCID 178481763HCID 178481763, 화합물수율 72.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매
HCID 8857
Ethyl Acetate
용매

실험 절차

In a flask, 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (trans-3-hydroxy-cyclobutyl)-amide (100 mg, 0.20 mmol) was dissolved in dichloromethane (1.0 mL). Trifluoroacetic acid (0.61 mL, 7.92 mmol) was added and the orange solution was stirred at room temperature for 2 h. The reaction mixture was concentrated. The residue (light orange foam) was suspended in dichloromethane (1.0 mL) and ethylenediamine (0.80 ml, 11.8 mmol) was added. The light yellow suspension was stirred at room temperature for 1 h. The reaction mixture was diluted with water and ethyl acetate. The suspension was filtered and washed with water (hot) and ethyl acetate. The resulting off-white powder was dried under high vacuum to provide 55 mg (66%; purity=90%) 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (trans-3-hydroxycyclobutyl)-amide. LC/MS: [M−H]−=379. 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 12.31-12.64 (br. s., 1H), 9.10 (s, 1H), 8.52 (dd, J=9.0, 5.2 Hz, 1H), 8.43 (s, 1H), 8.36 (d, J=7.1 Hz, 1H), 7.72 (dd, J=9.7, 2.1 Hz, 1H), 7.20 (td, J=9.1, 2.3 Hz, 1H), 5.19-5.26 (m, 1H), 4.52-4.61 (m, 1H), 4.44-4.61 (m, 1H), 4.16 (s, 3H), 2.25-2.40 (m, 4H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. stirringThe light yellow suspension was stirred at room temperature for 1 h
  3. filtrationThe suspension was filtered
  4. washwashed with water (hot) and ethyl acetate
  5. customThe resulting off-white powder was dried under high vacuum

출처 및 근거

ORD 기록
ord-0e1f3160c9be430c86a7e830ba88bff5
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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