1,2-Dichloroethane → HCID 86650852, 화합물

HRID 2189458노트

반응식

HRID 2189458 반응식
[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

참가 물질

8

반응물 5

HCID 111,2-Dichloroethane2회HCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole2회HCID 3214302-Chloro-3-hydrazinopyrazineHCID 58137752HCID 58137752, 화합물

생성물 1

HCID 86650852HCID 86650852, 화합물수율 74%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9b93c2a439c54fba998f07f865ea8108
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324241B2

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