1,2-Dichloroethane → HCID 86650849, compound

HRID 2189446Notes

Reaction equation

HRID 2189446 reaction equation
[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.[NH:35]([C:37]1[N:47]=[CH:46][CH:45]=[CH:44][C:38]=1[C:39]([O:41][CH2:42][CH3:43])=[O:40])[NH2:36].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:36][NH:35][C:37]4[N:47]=[CH:46][CH:45]=[CH:44][C:38]=4[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:16])=[CH:17][CH:18]=3)[S:8][C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 111,2-Dichloroethane2×HCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole2×HCID 53404568HCID 53404568, compoundHCID 58137752HCID 58137752, compound

Product 1

HCID 86650849HCID 86650849, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-(6-chlorobenzo[d]thiazol-2-ylamino)benzoic acid (117 mg, 0.38 mmol), EDC (88 mg, 0.46 mmol) and HOBt (63 mg, 0.46 mmol) in a mixed solvent of DMF (1 mL) and CH2Cl2 (1 mL) was stirred for 5 min, and then ethyl 2-hydrazinylnicotinate (4A) (70 mg, 0.38 mmol) was added, followed by triethylamine (78 mg, 0.77 mmol). The mixture was stirred at room temperature for 2 h. Analysis by LC/MS indicated the starting material was not consumed. Additional EDC (20 mg, 0.1 mmol) and HOBt (15 mg, 0.11 mmol) were added, and the mixture stirred for another 2 h before quenching with water (3 mL). The resulting precipitate was isolated by filtration and triturated with MeOH to yield the title compound as a fluffy white solid (94 mg). The methanol solution was concentrated in vacuo to collect additional product (50 mg) (total 144 mg, 87% yield). HPLC/MS (Method C): retention time=2.23 min, [M+H]+=468.4.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. customwas not consumed
  3. stirringthe mixture stirred for another 2 h
  4. custombefore quenching with water (3 mL)
  5. customThe resulting precipitate was isolated by filtration
  6. customtriturated with MeOH

Sources & evidence

ORD record
ord-996084e8df684c2d988b1876960a3627
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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