(1,1'-Biphenyl)-4-carboxylic acid → N-(4-(pyridazin-4-yl)benzyl)biphenyl-4-carboxamide

HRID 711216Notes

Reaction equation

HRID 711216 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=2)=[CH:3][N:2]=1.[C:15]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CS(C)=O>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:21]([C:18]3[CH:19]=[CH:20][C:15]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:16][CH:17]=3)=[O:22])=[CH:9][CH:8]=2)=[CH:3][N:2]=1

Participants

7

Reactant 4

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67208670(4-(Pyridazin-4-yl)phenyl)methanamine

Product 1

HCID 56597948N-(4-(pyridazin-4-yl)benzyl)biphenyl-4-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of (4-(pyridazin-4-yl)phenyl)methanamine 1-3 (19 mg, 0.1 mmol), biphenyl-4-carboxylic acid 1-4 (20 mg, 0.1 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (38 mg, 0.1 mmol) in DMF (0.5 mL) was added DIEA (0.052 mL, 0.3 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted into DMSO and purified by HPLC to give N-(4-(pyridazin-4-yl)benzyl)biphenyl-4-carboxamide 1 as a white solid. MS m/z 366.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ9.59 (m, 1H), 9.21 (dd, 1H), 9.16 (t, 1H), 7.96 (m, 3H), 7.87 (d, 2H), 7.74 (d, 2H), 7.69 (m, 2H), 7.47-7.41 (m, 4H), 7.37 (m, 1H), 4.52 (d, 2H).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-fb5d7c9c48684c9c8dfcff7bc5e6a7d4
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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