(E)-tert-Butyl 3-(3-(hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)propylcarbamate → (E)-N1-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)propane-1,3-diamine

HRID 1162145노트

반응식

HRID 1162145 반응식
[CH:1](/[C:7]1[N:11]2[N:12]=[C:13]([NH:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)=[CH:2]\[CH2:3][CH2:4][CH2:5][CH3:6]>C(O)(C(F)(F)F)=O>[CH:1](/[C:7]1[N:11]2[N:12]=[C:13]([NH:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)=[CH:2]\[CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

3

반응물 1

HCID 86621015(E)-tert-Butyl 3-(3-(hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)propylcarbamate

생성물 1

HCID 59519547(E)-N1-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)propane-1,3-diamine수율 29%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

The product from step B was stirred in TFA (3 mL) for 3 h. The reaction mixture was concentrated and partitioned between ethyl acetate and saturated sodium carbonate solution and the organic layer removed and concentrated. Purification by column chromatography (12 g ISCO column eluting with methylene chloride and methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 70% methylene chloride over 30 min at 25 mL/min) provided the title compound (26 mg, 29%) as a yellow solid; 1H NMR (500 MHz, CD3OD) δ 7.56 (d, J=9.6 Hz, 1H), 7.45 (s, 1H), 6.69-6.61 (m, 3H), 3.51 (t, J=6.4 Hz, 2H), 3.07 (t, J=7.4 Hz, 2H), 2.29-2.27 (m, 2H), 2.06 (m, 2H), 1.50-1.43 (m, 4H), 0.96 (t, J=7.1 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 155.3, 133.2, 128.8, 128.6, 125.7, 116.7, 113.6, 39.5, 39.0, 34.4, 32.9, 27.9, 23.4, 14.3 (one aromatic carbon overlapping); HPLC tR=10.9 min (Luna), 94.7%; ES-MS: (M+H)=274 m/z.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and saturated sodium carbonate solution
  3. customthe organic layer removed
  4. concentrationconcentrated
  5. customPurification
  6. washby column chromatography (12 g ISCO column eluting with methylene chloride and methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 70% methylene chloride over 30 min at 25 mL/min)

출처 및 근거

ORD 기록
ord-ca078dcac7f04ec58889b539d5961ebe
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820670B2

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