Diisopropylethylamine → HCID 76071821, compound

HRID 2275870Notes

Reaction equation

HRID 2275870 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH:57]1([N:60]2[CH:65]3[CH2:66][CH2:67][CH2:68][CH:61]2[CH2:62][CH:63]([NH2:69])[CH2:64]3)[CH2:59][CH2:58]1>CN(C=O)C.O>[CH:57]1([N:60]2[CH:65]3[CH2:66][CH2:67][CH2:68][CH:61]2[CH2:62][CH:63]([NH:69][C:16]([C:12]2[N:8]4[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]5[C:2]([F:1])=[CH:22][CH:21]=[CH:20][C:19]=5[F:23])[C:7]4=[N:14][C:13]=2[CH3:15])=[O:18])[CH2:64]3)[CH2:59][CH2:58]1

Participants

7

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 457926741210659-07-6HCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 76071821HCID 76071821, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

70 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid (0.22 mmol), 209 mg of O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU, 0.55 mmol) and 85 mg of N,N-diisopropylethylamine (0.66 mmol) were initially charged in 1.5 ml of DMF and stirred for 15 min. 59 mg of 9-cyclopropyl-9-azabicyclo[3.3.1]nonane-3-amine (0.33 mmol) were added, and the mixture was stirred at RT overnight. The mixture was then stirred overnight once more, at 60° C. 12 ml of water were added to the reaction solution, and the precipitate formed was filtered off, washed with water and dried. The residue formed was purified by silica gel chromatography (mobile phase: dichloromethane/methanol 40:1). This gave 60 mg of the title compound (53% of theory, purity 94%).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. stirringThe mixture was then stirred overnight once more
  3. customat 60° C
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried
  8. customThe residue formed
  9. customwas purified by silica gel chromatography (mobile phase: dichloromethane/methanol 40:1)

Sources & evidence

ORD record
ord-4cec4d377f5b41c2b158d003c205a051
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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