Diisopropylethylamine → HCID 59200037, compound

HRID 2382139Notes

Reaction equation

HRID 2382139 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N: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.[F:17][C:18]1[N:23]=[C:22]2[C:24]([CH3:28])=[CH:25][N:26]([NH2:27])[C:21]2=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:17][C:18]1[N:23]=[C:22]2[C:24]([CH3:28])=[CH:25][N:26]([NH:27][C:14]([C:10]3[C:11]([CH3:13])=[N:12][C:7]([C:2]4[N:1]=[CH:6][CH:5]=[CH:4][N:3]=4)=[N:8][CH:9]=3)=[O:16])[C:21]2=[CH:20][CH:19]=1

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 616999854-Methyl-2-(pyrimidin-2-yl)pyrimidine-5-carboxylic acidHCID 685521755-Fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine

Product 1

HCID 59200037HCID 59200037, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-pyrimidin-2-yl-4-methyl-pyrimidine-5-carboxylic acid (1.41 mmol), 5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine (1.41 mmol), DIPEA (158 mg, 4.22 mmol) and HATU (1.69 mmol) in anhydrous DMF (8 mL) is stirred at 90° C. for 16 hours. DMF is evaporated off in vacuo. The residue is dissolved in EtOAc (40 mL), washed with water (3×10 mL) and brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 1-20% MeOH in DCM to afford 4-methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide (125 mg) as a solid. MS: 364 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.31 (s, 3H), 2.87 (s, 3H), 6.87 (d, H), 7.50 (s, H), 7.66 (t, H), 7.96 (t, H), 9.04 (d, 2H), 9.27 (s, H).

Workup

  1. customDMF is evaporated off in vacuo
  2. dissolutionThe residue is dissolved in EtOAc (40 mL)
  3. washwashed with water (3×10 mL) and brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 1-20% MeOH in DCM

Sources & evidence

ORD record
ord-1a9700587e724dce98954d5db31b42d2
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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