Diisopropylethylamine → HCID 25099659, compound

HRID 2381939Notes

Reaction equation

HRID 2381939 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([OH:16])=O)=[CH:9][N:8]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:50][N:51]1[C:59]2[C:54](=[C:55]([F:60])[CH:56]=[CH:57][CH:58]=2)[CH:53]=[CH:52]1>CN(C=O)C>[F:60][C:55]1[CH:56]=[CH:57][CH:58]=[C:59]2[C:54]=1[CH:53]=[CH:52][N:51]2[NH:50][C:14]([C:10]1[C:11]([CH3:13])=[N:12][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:8][CH:9]=1)=[O:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 68553171HCID 68553171, compound

Product 1

HCID 25099659HCID 25099659, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(pyridine-2-yl)-4-methylpyrimidine-5-carboxylic acid (0.11 g) and HATU (0.19 g) in dry DMF (7 mL) is treated with DIPEA (0.09 mL) and stirred at rt under N2 for 30 min. 1-Amino-4-fluoroindole (0.112 g) is added and the mixture is stirred at rt for 24 h. The mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with water and brine and dried (MgSO4), filtered, and concentration in vacuo. The residue is purified by silica gel chromatography eluting with 75% EtOAc to afford 2-(pyridin-2-yl)-4-methylpyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amide (0.085 gms, 50%). MS: 348 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 2.82 (s, 3H), 6.65 (d, 1H), 6.93-6.97 (q, 1H), 7.19-7.26 (m, 1H), 7.35-7.38 (d, 1H), 7.62 (d, 1H), 7.74-7.78 (m, 1H), 8.20-8.25 (t, 1H), 8.58-8.61 (d, 1H), 8.85-8.86 (d, 1H), 9.33 (s, 1H), 12.15 (s, 1H).

Workup

  1. stirringthe mixture is stirred at rt for 24 h
  2. concentrationThe mixture is concentrated in vacuo
  3. dissolutionThe residue is dissolved in EtOAc
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentration in vacuo
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with 75% EtOAc

Sources & evidence

ORD record
ord-7d764bfdd5074132acf7734e7a4fc82f
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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