P-Anisidine → HCID 2146828, compound

HRID 1752789Notes

Reaction equation

HRID 1752789 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12][CH2:13][C:14]([OH:16])=O)[N:11]=[C:4]2[N:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12][CH2:13][C:14]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)=[O:16])[N:11]=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 714428Acetic acid, [(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)thio]-

Product 1

HCID 2146828HCID 2146828, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-({5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}sulfanyl)acetic acid (0.10 g, 0.42 mmol), p-anisidine (52 mg, 0.42 mmol), N,N-dicyclohexylcarbodiimide (87 mg, 0.42 mmol), and N,N-dimethylformamide (2 mL) was added to a 20 mL scintillation vial with a magnetic stirring bar. The mixture was allowed to stir at ambient temperature for 36 h. A white precipitate was removed by filtration and rinsed with N,N-dimethylformamide (0.5 mL) followed by water (1 mL). A precipitate formed in the liquid layer upon standing at ambient temperature for 12 h and was isolated by filtration. The crude precipitate was crystallized from warn ethanol (12 mL). The crystallized material was isolated by filtration, rinsed with ethanol, and allowed to dry. The title compound was obtained as an off-white solid (144 mg, 38% yield). 1H NMR (DMSO-d6, 400 MHz) δ ppm: 10.21 (s, 1H), 7.49 (d, 2H), 7.11 (s, 1H), 6.88 (d, 2H), 4.19 (s, 2H), 3.71 (s, 3H), 2.66 (s, 3H), 2.54 (s, 3H).

Workup

  1. additionwas added to a 20 mL scintillation vial with a magnetic stirring bar
  2. customA white precipitate was removed by filtration
  3. washrinsed with N,N-dimethylformamide (0.5 mL)
  4. customA precipitate formed in the liquid layer
  5. waitupon standing at ambient temperature for 12 h
  6. customwas isolated by filtration
  7. customThe crude precipitate was crystallized
  8. customThe crystallized material was isolated by filtration
  9. washrinsed with ethanol
  10. customto dry

Sources & evidence

ORD record
ord-5a8c5e5be1a64accb979e5662db80d6e
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

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