3-Pyridinemethanamine → 4-Amino-5-cyano-n-(pyridin-3-ylmethyl)-6-thien-3-ylpyridine-2-carboxamide

HRID 1364571Notes

Reaction equation

HRID 1364571 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[N:5]=[C:4]([C:15]([OH:17])=O)[CH:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH2:25])[CH:19]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(#N)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[N:5]=[C:4]([C:15]([NH:25][CH2:24][C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:3]=1

Participants

7

Reactant 4

HCID 310183-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669209934-Amino-5-cyano-6-thien-3-ylpyridine-2-carboxylic acid

Product 1

HCID 669209264-Amino-5-cyano-n-(pyridin-3-ylmethyl)-6-thien-3-ylpyridine-2-carboxamideYield 584.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of Example 266A (12 mg, 0.05 mmol), C-pyridin-3-yl-methylamine (6 μL, 0.1 mmol) in N,N-dimethylformamide (400 μL) was added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (17 mg, 0.053 mmol), followed by N,N-diisopropylethylamine (17 μL). The reaction mixture was stirred at ambient temperature for 3 hr. It was diluted with 1 mL acetonitrile and purified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to provide the titled compound as white solid (98 mg, 48%). 1H NMR (300 MHz, DMSO-d6) δ 9.35 (t, J=6.4 Hz, 1H), 8.56-8.38 (m, 3H), 7.93-7.90 (m, 1H), 7.74-7.66 (m, 2H), 7.40-7.32 (m, 3H), 7.36 (s, 1H), 4.52 (d, J=6.4 Hz, 2H). MS (m/e) 336 (M+H)+.

Workup

  1. custompurified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate)

Sources & evidence

ORD record
ord-2a9c22d7d0394261abee7eb13c2cfaf4
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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