Triethylamine → HCID 19085297, compound

HRID 963062Notes

Reaction equation

HRID 963062 reaction equation
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:34][CH2:35][C:36]1[N:40]([C:41]2[S:42][C:43]([CH2:55][CH3:56])=[CH:44][C:45]=2[C:46](=[O:54])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[Cl:53])[C:39]([CH3:57])=[N:38][N:37]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C:46]([C:45]1[CH:44]=[C:43]([CH2:55][CH3:56])[S:42][C:41]=1[N:40]1[C:39]([CH3:57])=[N:38][N:37]=[C:36]1[CH2:35][NH:34][C:1](=[O:11])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:54]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 444539Cinnamic AcidHCID 190850953-Aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole ditosylate

Product 1

HCID 19085297HCID 19085297, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

trans-Cinnamic acid (1.48 g), 3-aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole di-p-toluenesulfonate (7.42 g) and triethylamine (5.6 ml) were dissolved in dimethylformamide (50 ml). 1-Benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate (Bop reagent, 4.42 g) was added, and the mixture was stirred for one day. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated to give 5.05 g of crude crystals. The crystals were recrystallized from ethyl acetate to give 3.25 g of trans-N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3-phenylacrylamide.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customto give 5.05 g of crude crystals
  6. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-274aaa9941524f65901765735e884128
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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