Triethylamine → N-[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-2-(6-ethoxy-benzothiazol-2-ylsulfanyl)-acetamide

HRID 638808Notes

Reaction equation

HRID 638808 reaction equation
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]=[C:9]([S:11][CH2:12][C:13]([OH:15])=O)[S:10][C:6]=2[CH:5]=1)[CH3:2].C(N(CC)CC)C.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.[B-](F)(F)(F)F.CCCC[P+](C1SC(C(OC)=O)=C(C(OC)=O)S1)(CCCC)CCCC.[Cl:73][C:74]1[CH:75]=[C:76]([CH:84]=[CH:85][C:86]=1[Cl:87])[CH2:77][N:78]1[CH2:81][CH:80]([CH2:82][NH2:83])[CH2:79]1>ClCCl>[Cl:73][C:74]1[CH:75]=[C:76]([CH:84]=[CH:85][C:86]=1[Cl:87])[CH2:77][N:78]1[CH2:81][CH:80]([CH2:82][NH:83][C:13](=[O:15])[CH2:12][S:11][C:9]2[S:10][C:6]3[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:17]=[CH:16][C:7]=3[N:8]=2)[CH2:79]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 498382(4,5-Bis-methoxycarbonyl-[1,3]dithiol-2-yl)-tributyl-phosphoniumHCID 9419442-[(6-Ethoxy-1,3-benzothiazol-2-yl)sulfanyl]acetic acidHCID 68712490HCID 68712490, compound

Product 1

HCID 11511612N-[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-2-(6-ethoxy-benzothiazol-2-ylsulfanyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (6-Ethoxy-benzothiazol-2-ylsulfanyl)-acetic acid (0.087 g, 0.326 mmol) in dichloromethane (3 ml) is treated with triethylamine (0.041 ml, 0.326 mmol) and [(Benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium; tetrafluoro borate (0.104 g, 0.326 mmol) and stirred at ambient temperature for 3 minutes. To the reaction mixture is added a solution of C-[1-(3,4-Dichloro-benzyl)-azetidin-3-yl]-methylamine (0.08 g, 3.26 mmol) in dichloromethane (1 ml), with stirred for a further 3 hours. The reaction mixture is partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 95:5 dichloromethane:methanol as eluent to afford N-[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-2-(6-ethoxy-benzothiazol-2-ylsulfanyl)-acetamide. [MH]+ 495.8.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate and sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. customevaporated
  4. customThe crude product is purified by flash silica chromatography

Sources & evidence

ORD record
ord-17c0b3c34226448882d4525003418973
Source dataset
uspto-grants-2010_04
Patent number
US07691841B2

Reaction notes

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