1,2-Dichloroethane → HCID 46193342, compound

HRID 1013086Notes

Reaction equation

HRID 1013086 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[NH:8][C:7](=[O:9])[C:6]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:5]=1.[NH2:15][C:16]1[S:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[C:17]=1[C:25](O)=[O:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C>[NH2:15][C:16]1[S:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[C:17]=1[C:25]([N:12]1[CH2:13][CH2:14][C:6]2([N:5]=[C:4]([CH2:3][S:2][CH3:1])[NH:8][C:7]2=[O:9])[CH2:10][CH2:11]1)=[O:26]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 179376112-Amino-1-benzothiophene-3-carboxylic acidHCID 67316499HCID 67316499, compound

Product 1

HCID 46193342HCID 46193342, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3A (1.0 equivalent) in DMF (0.12 M) along with a 2-aminobenzo[b]thiophene-3-carboxylic acid (1.0 equivalent) was treated with EDC (1.0 equivalent), HOBt (1.0 equivalent) and Et3N (2.0 equivalents) at rt. The reaction mixture was stirred until the reaction was complete as determined by LCMS analysis and then partitioned between ethyl acetate and water. Organic layers were washed with brine and dried over Na2SO4, and volatiles removed under reduced pressure. Residue purified by LCMS to afford 8-(2-aminobenzo[b]thiophene-3-carbonyl)-2-(methylthiomethyl)-1,3,8-triazaspiro[4.5]dec-1-en-4-one (2B).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washOrganic layers were washed with brine
  3. dry with materialdried over Na2SO4, and volatiles
  4. customremoved under reduced pressure
  5. customResidue purified by LCMS

Sources & evidence

ORD record
ord-295d71a96cfd49acb73f9b1dd1c7fddc
Source dataset
uspto-grants-2011_07
Patent number
US07981904B2

Reaction notes

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