Triethylamine → HCID 178425159, compound

HRID 1479723Notes

Reaction equation

HRID 1479723 reaction equation
[OH:1][C:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].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.[NH2:45][CH2:46][C:47]1[C:48]([OH:55])=[N:49][C:50]([CH3:54])=[CH:51][C:52]=1[CH3:53]>ClCCl>[OH:55][C:48]1[C:47]([CH2:46][NH:45][C:9](=[O:11])[C:8]2[CH:7]=[CH:6][C:5]([C:2]([OH:1])([CH3:3])[CH3:4])=[CH:13][CH:12]=2)=[C:52]([CH3:53])[CH:51]=[C:50]([CH3:54])[N:49]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2261224-(2-Hydroxypropan-2-yl)benzoic acidHCID 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 178425159HCID 178425159, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-hydroxypropan-2-yl)benzoic acid (0.09 g, 0.5 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.23 g, 0.61 mmol) in dichloromethane (10 mL) was added triethylamine (0.15 g, 1.5 mmol). The reaction mixture was stirred for 15 minutes at room temperature, then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.08 g, 0.53 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with water (20 mL), concentrated and purified by column chromatography (silica gel:dichloromethane:methanol=30:1) to give the pure product (0.11 g, 76%) as a white solid. LRMS (M+H+) m/z: calcd for 314.16. found 314. HPLC Purity (214 nm) 100%. 1H NMR (300 MHz, DMSO-d6) δ: 11.47 (s, 1H), 8.28-8.26 (m, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H), 5.86 (s, 1H), 5.08 (s, 1H), 4.29 (d, J=4.8 Hz, 2H), 2.17 (s, 3H), 2.11 (s, 3H), 1.41 (s, 6H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction
  3. washthe mixture was washed with water (20 mL)
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica gel:dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-3a8459d53b0e42fcb18481c8b93ed11c
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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