Diisopropylethylamine → HCID 59278419, compound

HRID 2198234Notes

Reaction equation

HRID 2198234 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=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.Cl.[CH3:54][S:55]([C:58]1[CH:63]=[C:62]([C@@H:64]([NH2:66])[CH3:65])[CH:61]=[CH:60][N:59]=1)(=[O:57])=[O:56].C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[CH3:54][S:55]([C:58]1[CH:63]=[C:62]([C@@H:64]([NH:66][C:17]([C:16]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C:12]=3[CH:13]=[N:14][CH:15]=2)=[O:19])[CH3:65])[CH:61]=[CH:60][N:59]=1)(=[O:57])=[O:56]

Participants

8

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592781371-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acidHCID 66727499HCID 66727499, compound

Product 1

HCID 59278419HCID 59278419, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (17.74 g, 68.98 mmol) in DMF (200 mL) was added DIPEA (30 mL, 170 mmol) followed by HATU (27.37 g, 71.98 mmol). After 5 minutes, a light brown precipitate formed and additional DMF (50 mL) was added to aid stifling. After 1.5 hours, (S)-1-(2-methanesulfonyl-pyridin-4-yl)-ethylamine hydrochloride (14.20 g, 59.99 mmol) was added, followed by additional DIPEA (10 mL, 55 mmol). After 18 hours, the mixture was poured into water (1.5 L) containing sodium bicarbonate (25 g). The solid was collected by filtration and washed with aqueous sodium carbonate (1 L), water (1 L) and dried by pulling vacuum through the filter cake. The crude product was passed through a pad of silica gel eluting with EtOAc in dichloromethane (1:9, then 2:8, then 5:5, then 100:0). The material from the pad was concentrated and triturated with diethylether to afford the title compound as an off-white solid.

Workup

  1. customa light brown precipitate formed
  2. waitAfter 1.5 hours
  3. waitAfter 18 hours
  4. filtrationThe solid was collected by filtration
  5. washwashed with aqueous sodium carbonate (1 L), water (1 L)
  6. customdried
  7. concentrationThe material from the pad was concentrated
  8. customtriturated with diethylether

Sources & evidence

ORD record
ord-52239044ce3343c5bbc64ae810ba2d12
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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