Diisopropylethylamine → 6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 402378Notes

Reaction equation

HRID 402378 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:4]=[N:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:55][CH:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>CN(C=O)C>[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:55][CH:56]3[CH2:61][CH2:60][O:59][CH2:58][CH2:57]3)=[O:15])=[CH:11][N:10]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:4]=[N:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 674982816-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 573346476-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamideYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid (76 mg, 0.24 mmol) and TBTU (86 mg, 0.27 mmol) in DMF (1.2 mL) was added DIPEA (209 μL, 1.22 mmol). Then 4-aminotetrahydropyran (27 mg, 0.27 mmol) was added and the mixture was stirred at room temperature under Ar for 1 h. The mixture was then evaporated and purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) afforded the title compound (67 mg, 70%) as a white solid after recrystallisation from methanol/water. MS: m/e=395.1 [M+H]+.

Workup

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 50 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-7b1f2ed640d8402389681398d322242d
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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