(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 1162145ノート

反応式

HRID 1162145 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ca078dcac7f04ec58889b539d5961ebe
出典データセット
uspto-grants-2010_10
特許番号
US07820670B2

反応ノート

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