Triethylamine → HCID 178425216, compound

HRID 1501001Notes

Reaction equation

HRID 1501001 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:50][CH2:51][C:52]1[C:53]([OH:60])=[N:54][C:55]([CH3:59])=[CH:56][C:57]=1[CH3:58]>ClCCl>[OH:60][C:53]1[C:52]([CH2:51][NH:50][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])=[CH:18][CH:17]=2)=[C:57]([CH3:58])[CH:56]=[C:55]([CH3:59])[N:54]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79322Benzoic acid, 4-(phenylsulfonyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178425242HCID 178425242, compound

Product 1

HCID 178425216HCID 178425216, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(phenylsulfonyl)benzoic acid (80 mg, 0.3 mmol) in dichloromethane (15 mL) was added 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (171 mg, 0.45 mmol) and triethylamine (61 mg, 0.6 mmol), stirred for 30 minutes. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (50 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was washed with water (10 mL), dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by prep-TLC (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(phenylsulfonyl)benzamide as a light yellow solid (108 mg, 90.7%). LRMS (M+H+) m/z: calcd 396.11. found 396. HPLC purity (214 nm): 99%. 1H NMR (300 MHz, d6-DMSO): δ 11.50 (s, 1H), 8.63 (t, J=4.8 Hz, 1H), 8.03-7.98 (m, 6H), 7.76-7.63 (m, 3H), 5.88 (s, 1H), 4.31 (d, J=4.8 Hz, 2H), 2.17 (s, 3H), 2.13 (s, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washThe mixture was washed with water (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe residue was purified by prep-TLC (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-5d9931eaecbb49028177e35d1914fbd5
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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