Diisopropylamine → 3-Methyl-N-(1-{[2-(phenyloxy)phenyl]methyl}-1H-pyrazol-3-yl)-4-Pyridinecarboxamide

HRID 1946407Notes

Reaction equation

HRID 1946407 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[CH:34]=[N:33][CH:32]=[CH:31][C:27]=1[C:28]([OH:30])=O.C(NC(C)C)(C)C.[C:42]1([O:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH2:55][N:56]2[CH:60]=[CH:59][C:58]([NH2:61])=[N:57]2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C)C=O>[CH3:25][C:26]1[CH:34]=[N:33][CH:32]=[CH:31][C:27]=1[C:28]([NH:61][C:58]1[CH:59]=[CH:60][N:56]([CH2:55][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2[O:48][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:57]=1)=[O:30]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 15020033-Methyl-isonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595480071-{[2-(Phenyloxy)phenyl]methyl}-1H-pyrazol-3-amine

Product 1

HCID 595479303-Methyl-N-(1-{[2-(phenyloxy)phenyl]methyl}-1H-pyrazol-3-yl)-4-Pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of HATU (38 mg, 0.1 mmol) in N,N-dimethylformamide (0.3 ml) was added to 3-methyl-isonicotinic acid (14 mg, 0.1 mmol, AstaTech Inc) followed by N,N-diisopropylamine (0.050 ml, 0.286 mmol) and left to stand for 10 minutes at ambient temperature. A solution of 1-{[2-(phenyloxy)phenyl]methyl}-1H-pyrazol-3-amine (for a preparation see Intermediate 38)(27 mg, 0.101 mmol) in N,N-dimethylformamide (0.1 ml) was then added and the solution left to stand at room temperature overnight. Purification by MDAP (Method D) gave the title compound (20.2 mg); LCMS: (System 1) MH+=385, tRET=0.93 min.

Workup

  1. waitleft
  2. additionwas then added
  3. waitthe solution left
  4. waitto stand at room temperature overnight
  5. customPurification by MDAP (Method D)

Sources & evidence

ORD record
ord-a4ecbedb4d9140eca565503565ff8a1c
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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