Triethylamine → HCID 58609757, compound

HRID 1673114Notes

Reaction equation

HRID 1673114 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([OH:15])=O)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.S(Cl)(Cl)=O.C(N(CC)CC)C.[NH2:27][C:28]1[S:29][C:30]([C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:41])=[O:34])=[CH:31][N:32]=1>O1CCOCC1.CN(C)C=O>[Cl:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:33]([C:30]1[S:29][C:28]([NH:27][C:13]([C:10]2([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH2:11][CH2:12]2)=[O:15])=[N:32][CH:31]=1)=[O:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acidHCID 574569435-[(2-Chlorophenyl)carbonyl]-1,3-thiazol-2-amine

Product 1

HCID 58609757HCID 58609757, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid (1.29 g, 6.28 mmol) was placed in an oven-dried flask under nitrogen. Thionyl chloride (3 mL) and N,N-dimethylformamide (0.3 mL) were added and the solution was allowed to stir for 2 hours. The excess thionyl chloride was removed under vacuum and the resulting solid was suspended in 30 mL of anhydrous 1,4-dioxane containing triethylamine (1.77 mL, 12.6 mmol). (2-Amino-thiazol-5-yl)-(2-chloro-phenyl)-methanone (1.50 g, 6.28 mmol) suspended in 10 mL of anhydrous 1,4-dioxane was slowly added to this suspension. The resulting suspension was allowed to stir for 20 minutes. The mixture was filtered and then the filtrate was evaporated to dryness. The crude product was dissolved in 50 mL of dichloromethane and washed three times with 50 mL of 1N HCl, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was then dried over sodium sulfate and evaporated to dryness to yield the product as a beige solid (1.51 g, 3.54 mmol, 56.4%). 1H NMR (400 MHz, DMSO-d6) δ 1.20-1.24 (m, 2H), 1.54-1.57 (m, 2H), 6.01 (s, 2H), 6.88 (d, J=1.3 Hz, 2H), 6.98 (s, 1H), 7.48-7.52 (m, 1H), 7.56-7.60 (m, 3H), 7.77 (s, 1H), 11.98 (s, 1H). ESI-MS m/z calc. 426.0. found; 427.3 (M+1)+; Retention time 3.46 minutes.

Workup

  1. customThe excess thionyl chloride was removed under vacuum
  2. additionwas slowly added to this suspension
  3. stirringto stir for 20 minutes
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe crude product was dissolved in 50 mL of dichloromethane
  7. washwashed three times with 50 mL of 1N HCl, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  8. dry with materialThe organic layer was then dried over sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-1067b80c0ad848759282b062fd296273
Source dataset
uspto-grants-2011_08
Patent number
US07999113B2

Reaction notes

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