p-Toluenesulfonic acid → N-(4-Pentafluoroethyl-phenyl)-2-[(pyrimidin-4-ylmethyl)-amino]-nicotinamide

HRID 1815202Notes

Reaction equation

HRID 1815202 reaction equation
[NH2:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)=[O:5].CC1C=CC(S(O)(=O)=O)=CC=1.[N:35]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[N:37][CH:36]=1.[BH4-].[Na+]>CS(C)=O>[F:19][C:13]([F:18])([C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:20]=[CH:21][CH:22]=[N:23][C:2]=2[NH:1][CH2:41][C:38]2[CH:39]=[CH:40][N:35]=[CH:36][N:37]=2)=[CH:8][CH:9]=1)[C:14]([F:15])([F:16])[F:17]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 11412355Pyrimidine-4-carboxaldehydeHCID 222493922-Amino-N-(4-pentafluoroethyl-phenyl)-nicotinamide

Product 1

HCID 22249292N-(4-Pentafluoroethyl-phenyl)-2-[(pyrimidin-4-ylmethyl)-amino]-nicotinamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Amino-N-(4-pentafluoroethyl-phenyl)-nicotinamide (180 mg), TsOH (40 mg) and a solution of pyrimidine-4-carboxaldehyde in DMSO (10 ml) were stirred at 60 C. for 6 h. Treated with NaBH4 (200 mg) and stirred for 2 h at RT. MS (ES+): 566.3 (M+H)+; Calc'd for C26H28F5N7O2—565.

Sources & evidence

ORD record
ord-2446b15df7364f6db32ddf81857866d4
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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