3-Pyridinemethanamine → 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 2080274Notes

Reaction equation

HRID 2080274 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:10]=1)#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH2:62][CH2:63][C:64]1[CH:65]=[N:66][CH:67]=[CH:68][CH:69]=1>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:62][CH2:63][C:64]2[CH:65]=[N:66][CH:67]=[CH:68][CH:69]=2)=[O:14])=[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:10]=1)#[N:2]

Participants

6

Reactant 4

HCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 575423046-(2-Cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid

Product 1

HCID 575425256-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (2.8 g, 7.76 mmol) in DMF (28 mL) was added HBTU (5.88 g, 15.51 mmol), HOBt (2.1 g, 15.51 mmol), then 3-aminomethylpyridine (1.68 g, 15.51 mmol). The reaction mixture was stirred at room temperature for 1 hr. The crude mixture was purified on RP-HPLC using a mixture of acetonitrile and H2O to give 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide as a pale yellow solid (3.0 g, 86%). LRMS (M+H+) m/z 452.2.

Workup

  1. customThe crude mixture was purified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-92951b79cf314a19ae14e576c1f48539
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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