Triethylamine → HCID 46181767, compound

HRID 2380974Notes

Reaction equation

HRID 2380974 reaction equation
[CH2:1]([N:8]([S:18]([C:21]1[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=1)(=[O:20])=[O:19])[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH2:1]([N:8]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:31]2[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]2)=[O:14])=[CH:11][CH:10]=1)[S:18]([C:21]1[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=1)(=[O:19])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67134151HCID 67134151, compound

Product 1

HCID 46181767HCID 46181767, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-[benzyl-(1-methyl-1H-imidazole-4-sulfonyl)-amino]-benzoic acid (37 mg, 0.1 mmol) in dry dimethylformamide (1 ml) was added N-methylpiperazine (20 mg, 0.2 mmol), triethylamine (28 μl, 0.2 mmol) then 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (42 mg, 0.11 mmol) and the solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and the residue purified using preparative HPLC to afford the title compound as a clear oil (30 mg, 66% HPLC retention time 4.5 min. Mass spectrum (ES+) m/z 454 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified

Sources & evidence

ORD record
ord-e1bc19f97b44465485bbae9884decd37
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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