p-Toluidine → HCID 86640692, compound

HRID 2176112Notes

Reaction equation

HRID 2176112 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 86640692HCID 86640692, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 500 mL round-bottom flask were combined 2-(6-chloropyridin-3-yl)acetic acid (10.3 g, 60.0 mmol; Oakwood), p-toluidine (6.43 g, 60.0 mmol; Aldrich) and N,N-diisopropylethylamine (34.3 mL, 198 mmol; Aldrich) in tetrahydrofuran (220 mL). The mixture was stirred at room temperature for 1 hour, and then O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU; 25.1 g, 66.0 mmol; Aldrich) was added. After 16 hours, the reaction was concentrated, the residue dissolved in ethyl acetate (500 mL) and washed with water (50 mL). The organic phase was concentrated and purified by flash chromatography (silica gel, hexanes/ethyl acetate, 2:1) to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.28 (s, 3H), 3.71 (s, 2H), 7.11 (d, J=8 Hz, 2H), 7.37-7.46 (m, 3H), 7.81 (dd, J=8, 3 Hz, 1H), 8.33 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 261 (M+H)+.

Workup

  1. customIn a 500 mL round-bottom flask were combined
  2. waitAfter 16 hours
  3. concentrationthe reaction was concentrated
  4. dissolutionthe residue dissolved in ethyl acetate (500 mL)
  5. washwashed with water (50 mL)
  6. concentrationThe organic phase was concentrated
  7. custompurified by flash chromatography (silica gel, hexanes/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-760775a8024d46e5916d0b4bfa6e772b
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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