1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 89705069, compound

HRID 929043Notes

Reaction equation

HRID 929043 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.[CH:44]([O:46][CH2:47][CH2:48][O:49][NH2:50])=[CH2:45].[NH4+].[Cl-]>C(Cl)Cl>[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([NH:50][O:49][CH2:48][CH2:47][O:46][CH:44]=[CH2:45])=[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]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 89705389HCID 89705389, compound

Product 1

HCID 89705069HCID 89705069, compoundYield 79.7%

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 (200 mg, 0.49 mmol) in CH2Cl2 (10 mL) was added HOBt (100 mg, 0.69 mmol) and EDCI (140 mg, 0.69 mmol). The mixture was stirred for 1 h and O-(2-(vinyl-oxy)ethyl)hydroxylamine (72 mg, 0.69 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 were washed with water (10 mL) and brine (10 mL), dried over Na2SO4 filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1, v/v) and gave the desired product (yellow solid, 190 mg, 79.7% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.85 (s, 1H), 8.65 (s, 1H), 8.51 (s, 1H), 7.38 (d, 1H), 7.29 (d, 1H), 6.64 (dd, 1H), 6.42 (d, 1H), 4.21 (d, 1H), 4.01 (m, 3H), 3.83 (m, 2H).

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 were washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1

Sources & evidence

ORD record
ord-4b853edd95334744b971fed4039e2bf4
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

Loading…