1,2-Dichloroethane → HCID 25072229, compound

HRID 387366Notes

Reaction equation

HRID 387366 reaction equation
[O:1]=[S:2]1(=[O:27])[CH2:8][CH2:7][CH2:6][CH:5]([C:9]2[C:17]3[C:12](=[C:13]([C:24]([OH:26])=O)[CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:16]=3)[NH:11][CH:10]=2)[CH2:4][CH2:3]1.C1C=CC2N(O)N=[N:34]C=2C=1.C(Cl)CCl.N>O1CCOCC1>[O:1]=[S:2]1(=[O:27])[CH2:8][CH2:7][CH2:6][CH:5]([C:9]2[C:17]3[C:12](=[C:13]([C:24]([NH2:34])=[O:26])[CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:16]=3)[NH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 59332798HCID 59332798, compound

Product 1

HCID 25072229HCID 25072229, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

3-(1,1-Dioxido-4-thiepanyl)-5-phenyl-1H-indole-7-carboxylic acid (0.076 mmol), HOBT (10 mg, 0.074 mmol), EDC (15 mg, 0.078 mmol) were mixed together. A solution of 0.5 M NH3 in dioxane (1.5 mL) was added in, and the reaction was heated in a microwave at 120° C. for 10 minutes, then allowed to sit at room temperature overnight. The solvent was evaporated and the crude product was dissolved in DMSO and purified by Gilson HPLC (0.1% TFA, 10%-90% CH3CN, 10 minutes). The desired fractions were concentrated, giving 4 mg of the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude product was dissolved in DMSO
  3. custompurified by Gilson HPLC (0.1% TFA, 10%-90% CH3CN, 10 minutes)
  4. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-2c0a5cf116e242dbbba89929e3a69f12
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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