Diisopropylethylamine → HCID 178522176, compound

HRID 555906Notes

Reaction equation

HRID 555906 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)=[C:6]([CH:8]=1)[NH2:7].C(N(C(C)C)CC)(C)C.[Cl:23][C:24]1[CH:28]=[CH:27][S:26][C:25]=1[C:29](Cl)=[O:30]>ClCCl>[Cl:23][C:24]1[CH:28]=[CH:27][S:26][C:25]=1[C:29]([NH:7][C:6]1[CH:8]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:9]1[NH:13][N:12]=[N:11][N:10]=1)=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27358243-Chlorothiophene-2-carbonyl chlorideHCID 178507674HCID 178507674, compound

Product 1

HCID 178522176HCID 178522176, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The intermediate 5-chloro-2-(1H-tetrazol-5-yl)aniline (200 mg, 1.0 mmol) and diisopropylethylamine (310 uL, 1.7 mmol) were taken up in 5 mL of dichloromethane. To the solution was added 3-chlorothiophene-2-carboyl chloride (221 mg, 1.2 mmol). The solution was stirred for 4 hours, at which point starting material was no longer detected by LCMS analysis. Dichloromethane (10 ml) was then added to solution. This solution was extracted 3 times with an aqueous solution of 0.1 N NaOH. The aqueous extractions were combined and concentrated HCl was added to until pH=1. The resulting precipitate was filtered and washed with acetonitrile to yield final product (141.1 mg, 41%). 1H NMR (400 MHz, d6-DMSO): 11.89 (s, 1H), 8.60 (s, 1H), 8.26 (d, 1H), 8.05 (d, 1H), 7.45 (d, 1H), 7.30 (d, 1H). MS (EI) for C12H7Cl2N5OS: 340.2 (M+H).

Workup

  1. extractionThis solution was extracted 3 times with an aqueous solution of 0.1 N NaOH
  2. extractionThe aqueous extractions
  3. additionconcentrated HCl was added to until pH=1
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with acetonitrile

Sources & evidence

ORD record
ord-8487e8fa572441098703e0f062045019
Source dataset
uspto-grants-2011_11
Patent number
US08053454B2

Reaction notes

Loading…