Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 22439207, compound

HRID 963105Notes

Reaction equation

HRID 963105 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1/[CH:10]=[CH:11]/[C:12]([OH:14])=O)([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:37][CH2:38][C:39]1[N:43]([C:44]2[S:45][C:46]([CH2:58][CH3:59])=[CH:47][C:48]=2[C:49](=[O:57])[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[Cl:56])[C:42]([CH3:60])=[N:41][N:40]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(N(CC)CC)C>[Cl:56][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=1[C:49]([C:48]1[CH:47]=[C:46]([CH2:58][CH3:59])[S:45][C:44]=1[N:43]1[C:42]([CH3:60])=[N:41][N:40]=[C:39]1[CH2:38][NH:37][C:12](=[O:14])/[CH:11]=[CH:10]/[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[O:57]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7359232-Nitrocinnamic acidHCID 190850953-Aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole ditosylate

Product 1

HCID 22439207HCID 22439207, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Reaction was carried out in the same manner as in Example 186 using trans-3-(2-nitrophenyl)propenoic acid (1.93 g), 3-aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole di-p-toluenesulfonate (7.42 g), triethylamine (5.6 ml) and 1-benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate (Bop reagent, 4.42 g), and the obtained crude crystals were recrystallized from ethyl acetate to give 3.65 g of trans-N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3-(2-nitrophenyl)propenamide.

Workup

  1. customReaction
  2. customthe obtained crude crystals
  3. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6a7178dce2e64e32ad1a1c8ad601b52b
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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