1,2-Dichloroethane → HCID 86650852、化合物

HRID 2189458ノート

反応式

HRID 2189458 の反応式
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:35][C:36]1[C:41]([NH:42][NH2:43])=[N:40][CH:39]=[CH:38][N:37]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:14]([NH:43][NH:42][C:41]4[C:36]([Cl:35])=[N:37][CH:38]=[CH:39][N:40]=4)=[O:16])=[CH:17][CH:18]=3)[S:8][C:4]=2[CH:3]=1

参加物

8

反応物 5

HCID 111,2-Dichloroethane2 回HCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole2 回HCID 3214302-Chloro-3-hydrazinopyrazineHCID 58137752HCID 58137752、化合物

生成物 1

HCID 86650852HCID 86650852、化合物収率 74%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of 4-(6-chlorobenzo[d]thiazol-2-ylamino)benzoic acid (63A) (6.62 g, 21.72 mmol), EDC (4.37 g, 22.81 mmol) and HOBt (3.08 mg, 22.81 mmol) in a mixed solvent of DMF (25 mL) and CH2Cl2 (50 mL) was stirred for 5 min, and then 2-chloro-3-hydrazinylpyrazine (61A) (3.14 g, 21.72 mmol) and triethylamine (4.4 g, 43.4 mmol) were added. The mixture was stirred at room temperature over the weekend. Additional EDC (1.5 g, 7.85 mmol) and HOBt (1.15 g, 8.45 mmol) were added in and the reaction mixture stirred for another 2 h before concentrated in vacuo. The obtained residue was partitioned between EtOAc (250 mL) and water (200 mL), and the separated EtOAc layer washed with water (2×200 mL), and concentrated in vacuo. The crude product was triturated with water (50 mL) and EtOAc (20 mL) and isolated by filtration, rinsed with water and then air dried to yield the title compound as a dark brown solid (6.17 g). The second crop of the product was isolated from the concentrated mother liquor using the same trituration process (0.76 g) (total 6.93 g, 74% yield). HPLC/MS (Method C): retention time=2.43 min, [M+H]+=431.1. 1H NMR (500 MHz, DMSO-d6) δ 10.90 (s, 1H), 10.41 (s, 1H), 9.12 (s, 1H), 8.09 (d, J=2.20 Hz, 1H), 7.99 (d, J=2.20 Hz, 1H), 7.91-7.97 (m, 2H), 7.85-7.90 (m, 2H), 7.78 (d, J=2.75 Hz, 1H), 7.65 (d, J=8.80 Hz, 1H), 7.37 (dd, J=8.80, 2.20 Hz, 1H).

後処理

  1. stirringThe mixture was stirred at room temperature over the weekend
  2. stirringstirred for another 2 h
  3. concentrationbefore concentrated in vacuo
  4. customThe obtained residue was partitioned between EtOAc (250 mL) and water (200 mL)
  5. washthe separated EtOAc layer washed with water (2×200 mL)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was triturated with water (50 mL) and EtOAc (20 mL)
  8. customisolated by filtration
  9. washrinsed with water
  10. customair dried

出典と根拠

ORDレコード
ord-9b93c2a439c54fba998f07f865ea8108
出典データセット
uspto-grants-2012_12
特許番号
US08324241B2

反応ノート

読み込み中…