Diisopropylethylamine → HCID 59200039, compound

HRID 2382101Notes

Reaction equation

HRID 2382101 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[N:4]([NH2:11])[CH:3]=1.[CH3:12][C:13]1[C:18]([C:19](O)=[O:20])=[CH:17][N:16]=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:14]=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.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[N:4]([NH:11][C:19]([C:18]2[C:13]([CH3:12])=[N:14][C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:16][CH:17]=2)=[O:20])[CH:3]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 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 68553177HCID 68553177, compound

Product 1

HCID 59200039HCID 59200039, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methyl-pyrrolo[2,3-c]pyridin-1-yl amine (467 mg, 3.18 mmol), 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (683 g, 3.18 mmol), HATU (1.45 g, 3.81 mmol), DIPEA (1.23 g 9.54 mmol) in DMF (10 mL) is stirred at 1500 C. for 1 h. The reaction is quenched with water, and NaHCO3 (320 mg, 3.81 mmol) and EtOAC are added. The resulting solid is collected by filtration and then triturated with hot water. The mixture is filtered again and the solid is dried under vacuum to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-c]pyridin-1-yl)-amide (484 mg). MS: 345 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.24 (s, 1H), 8.79 (d, 2H), 8.65 (d, 1H), 8.21 (d, 1H), 8.05 (t, 1H), 7.72 (d, 1H), 7.60 (s, 1H), 7.57 (s, 1H), 2.88 (s, 3H), 2.40 (s, 3H).

Workup

  1. additionare added
  2. filtrationThe resulting solid is collected by filtration
  3. customtriturated with hot water
  4. filtrationThe mixture is filtered again
  5. customthe solid is dried under vacuum

Sources & evidence

ORD record
ord-2c8c689d71324db9a0c1eb08a3828fd2
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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