1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 89705466, compound

HRID 929056Notes

Reaction equation

HRID 929056 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11](O)=[O:12])[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:44][C:45]1([CH3:53])[O:49][CH:48]([CH2:50][O:51][NH2:52])[CH2:47][O:46]1.[NH4+].[Cl-]>C(Cl)Cl>[CH3:44][C:45]1([CH3:53])[O:49][CH:48]([CH2:50][O:51][NH:52][C:11]([C:4]2[C:3]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[F:22])=[C:2]([F:1])[C:7]3[N:8]=[N:9][S:10][C:6]=3[CH:5]=2)=[O:12])[CH2:47][O:46]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 10240948O-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]hydroxylamineHCID 89705389HCID 89705389, compound

Product 1

HCID 89705466HCID 89705466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d][1,2,3]thiadiazole-6-carboxylic acid (210 mg, 0.48 mmol) in CH2Cl2 (10 mL) was added HOBt (105 mg, 0.72 mmol) followed by EDCI (138 mg, 0.72 mmol). The mixture was stirred for 1 h and O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine (108 mg, 0.74 mmol) was added. After stirring for 4 h at ambient temperature, the reaction was treated with saturated NH4Cl (aq.). The resultant mixture was extracted with CH2Cl2 (15 mL×3). The combined organic extracts was washed by water (10 mL) and brine (10 mL) sequentially, dried over Na2SO4, filtered and concentrated in vacuo. The crude product (229 mg) was used directly in the next step without further purification.

Workup

  1. stirringAfter stirring for 4 h at ambient temperature
  2. extractionThe resultant mixture was extracted with CH2Cl2 (15 mL×3)
  3. washThe combined organic extracts was washed by water (10 mL) and brine (10 mL) sequentially
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product (229 mg) was used directly in the next step without further purification

Sources & evidence

ORD record
ord-db2518c087a243609f0204b9045b3c4b
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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