2-Pyridinemethanamine → HCID 57520012, compound

HRID 1911674Notes

Reaction equation

HRID 1911674 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.F[B-](F)(F)F.[N:29]1(OC(N(C)C)=[N+](C)C)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=N1.C(N(CC)C(C)C)(C)C.NCC1C=CC=CN=1>CN(C=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:31][CH2:32][C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][N:29]=2)=[O:21])=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 57520012HCID 57520012, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.64 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (228 mg, 0.71 mmol), N,N-diisopropyl ethyl amine (552 μL, 3.22 mmol) and 2-(aminomethyl)pyridine (0.77 mmol). The resulting reaction mixture was stirred for 12 h at ambient temperature. After dilution with ethyl acetate (20 mL) it was washed with water (20 mL) and aqueous sodium carbonate (saturated, 40 mL). The organic layer was dried over sodium sulfate and concentrated. Purification by chromatography ((SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:95:5) afforded the title compound (191 mg, 74%) which was obtained as a white solid. MS: m/e=401.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. washAfter dilution with ethyl acetate (20 mL) it was washed with water (20 mL) and aqueous sodium carbonate (saturated, 40 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography ((SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:95:5)

Sources & evidence

ORD record
ord-22346b4dd8e140909156bf2c54eb091b
Source dataset
uspto-grants-2013_12
Patent number
US08604062B2

Reaction notes

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