2-Pyridinemethanamine → HCID 11737227, compound

HRID 2245540Notes

Reaction equation

HRID 2245540 reaction equation
C(N(C(C)C)C(C)C)C.[O:10]=[C:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]([OH:22])=O)[CH:17]=2)[NH:12]1.F[B-](F)(F)F.[N:28]1(OC(N(C)C)=[N+](C)C)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=N1.O.ON1C2C=CC=CC=2N=N1.NCC1C=CC=CN=1.C([O-])(O)=O.[Na+]>CN(C)C=O.C(#N)C>[O:10]=[C:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]([NH:30][CH2:31][C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][N:28]=3)=[O:22])[CH:17]=2)[NH:12]1

Participants

8

Reactant 6

HCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27733182-Oxindole-5-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 11737227HCID 11737227, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a N,N-dimethylformamide/acetonitrile, (2 mL: 10 mL), mixture containing ethyldiisopropylamine (0.52 mL, 3 mmol) was added 2-oxoindoline-5-carboxylic acid (0.354 g, 2.0 mmol; described in: Sun L. et al. J. Med. Chem. 2000, 43(14), 2655:), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.77 g, 2.4 mmol) and 1-hydroxybenzotriazole hydrate (0.324 g, 2.4 mmol) and stirred for 5 min at room temperature. Thereafter, 2-(aminomethyl)pyridine (0.562 g, 5.2 mmol) was added and the resulting reaction mixture was stirred for 90 min followed by addition of a saturated aqueous NaHCO3 solution (10 mL). The solvents were removed in vacuo and 0.364 g (68% yield) of the title product was obtained as a white solid after purification on a silica gel column using chloroform/methanol, (9:1), as the eluent: 1H NMR (DMSO-d6, 400 MHz) δ 10.66 (s, 1H), 8.96 (t, J=5.6 Hz, 1H), 8.55 (d, J=4.4 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.83 (s, 1H), 7.78 (t, J=7.6 Hz, 1H), 7.34 (d, J=8.0 Hz, 1H), 7.29 (t, J=6.4 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 4.59 (d, J=6.0 Hz, 2H), 3.58 (s, 2H); MS (EI) m/z 268 (M++1).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred for 90 min
  3. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-aa75092b33bf440189eb679894073812
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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