Phenyl isocyanate → 1-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-phenylurea

HRID 1426174ノート

反応式

HRID 1426174 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]2[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)[S:7][CH:8]=1.[N:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[C:25]=[O:26].C(OCC)(=O)C>CN(C=O)C>[CH2:17]([O:16][C:15]1[C:10]([NH:9][C:6]2[S:7][CH:8]=[C:4]([CH2:3][CH2:2][NH:1][C:25]([NH:24][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])[N:5]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 7672Phenyl isocyanateHCID 8857Ethyl AcetateHCID 866397044-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

生成物 1

HCID 592257051-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-phenylurea収率 35.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Crude 4-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine (Example 134, Step A; 0.25 g, 0.766 mmol) was dissolved in DMF (10 mL), and 1-isocyanatobenzene (0.182 g, 1.53 mmol) was added. The reaction mixture was stirred for 2 hours, then partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 2:3 hexane:ethyl acetate to afford the title compound (0.122 g, 35.8% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 2.75 (t, 2H), 3.42 (q, 2H), 5.27 (s, 2H), 6.19 (t, 1H), 6.70 (s, 1H), 6.86-6.91 (m, 2H), 7.20 (t, 2H), 7.34-7.43 (m, 6H), 7.58 (d, 2H), 7.87 (d, 1H), 8.48 (s, 1H), 9.94 (s, 1H).

後処理

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (Biotage)
  6. washeluting with 2:3 hexane

出典と根拠

ORDレコード
ord-3ff81066872e44c684118f44b94ed5dc
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

反応ノート

読み込み中…