Triethylamine → HCID 178425215, compound

HRID 1501011Notes

Reaction equation

HRID 1501011 reaction equation
[C:1]1([S:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][C:20]1[C:21]([OH:28])=[N:22][C:23]([CH3:27])=[CH:24][C:25]=1[CH3:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.O>[OH:28][C:21]1[C:20]([CH2:19][NH:18][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:8])=[CH:17][CH:16]=2)=[C:25]([CH3:26])[CH:24]=[C:23]([CH3:27])[N:22]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 3438114-Benzenesulfinyl-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 178425215HCID 178425215, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(phenylsulfinyl)benzoic acid (130 mg, 0.53 mmol), 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (100 mg, 0.6 mmol), o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1.0 mmol) and triethylamine (0.1 mL) in dichloromethane (6 mL) was stirred at 25° C. for 12 hours. After the reaction, water (10 mL) was added and the mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(phenylsulfinyl)benzamide as a white solid (90 mg, 44%). LRMS (M+H+) m/z: calcd 380.12. found 380. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.47 (t, J=4.8 Hz, 1H), 7.94 (d, J=8.7 Hz, 2H), 7.78-7.71 (m, 4H), 7.54-7.50 (m, 3H), 5.84 (s, 1H), 4.28 (d, J=4.8 Hz, 2H), 2.14 (s, 3H), 2.10 (s, 3H).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (10 mL×3)
  3. dry with materialThe combined organic phase was dried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-bcac65adaec14128a77dcf0f9d8a0efa
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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