1,2-Dichloroethane → HCID 44243000, compound

HRID 1013085Notes

Reaction equation

HRID 1013085 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]=[C:4]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[NH:3]1.[CH2:17]([NH:19][C:20](=[O:34])[NH:21][C:22]1[S:26][C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[C:23]=1[C:31](O)=[O:32])[CH3:18].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[CH2:17]([NH:19][C:20](=[O:34])[NH:21][C:22]1[S:26][C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[C:23]=1[C:31]([N:9]1[CH2:8][CH2:7][C:6]2([N:5]=[C:4]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[NH:3][C:2]2=[O:1])[CH2:11][CH2:10]1)=[O:32])[CH3:18]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 57908084HCID 57908084, compoundHCID 57908095HCID 57908095, compound

Product 1

HCID 44243000HCID 44243000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solutions each of 2B (1.0 equivalent), 2-(3-ethylureido)benzo[b]thiophene-3-carboxylic acid (2C, 1.25 equivalents), DMF (0.14 M), EDC (1.25 equivalents), and HOBT (1.25 equivalents) is added triethylamine (1.0 equivalent) at room temperature. After stirring for 12 hr, the reaction is complete as determined by LCMS analysis. The reaction mixture is then partitioned between ethyl acetate and water and the separated organics is dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by preparatory LCMS provides N-((8-(2-(3-ethylureido)benzo[b]thiophene-3-carbonyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-2-yl)methyl)acetamide (2), respectively.

Workup

  1. customThe reaction mixture is then partitioned between ethyl acetate and water
  2. dry with materialthe separated organics is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by preparatory LCMS

Sources & evidence

ORD record
ord-f4bbe372a6714cfdac95ca23bce6d63e
Source dataset
uspto-grants-2011_07
Patent number
US07981904B2

Reaction notes

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