Diisopropylethylamine → HCID 57749311, compound

HRID 1874519Notes

Reaction equation

HRID 1874519 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[N:11]=[C:10]2[S:12][C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])=[N:14][C:9]2=[CH:8][CH:7]=1.[CH3:24][N:25]1[CH:29]=[CH:28][N:27]=[C:26]1[C:30](O)=[O:31].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>O.CN(C)C=O>[CH:18]1([C:16]([NH:15][C:13]2[S:12][C:10]3[C:9]([N:14]=2)=[CH:8][CH:7]=[C:6]([O:5][C:4]2[CH:3]=[C:2]([NH:1][C:30]([C:26]4[N:25]([CH3:24])[CH:29]=[CH:28][N:27]=4)=[O:31])[CH:23]=[CH:22][CH:21]=2)[N:11]=3)=[O:17])[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5576781-methyl-1H-imidazole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57387081HCID 57387081, compound

Product 1

HCID 57749311HCID 57749311, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[5-(3-aminophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (175 mg, 0.536 mmol), 1-methyl-1H-imidazole-2-carboxylic acid (101 mg, 0.804 mmol), HATU (367 mg, 0.965 mmol), N,N-diisopropylethylamine (420 μL, 2.41 mmol) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=50/50→0/100) and recrystallized from ethyl acetate-tetrahydrofuran to give the title compound (152 mg, 65%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=50/50→0/100)
  7. customrecrystallized from ethyl acetate-tetrahydrofuran

Sources & evidence

ORD record
ord-7b8d066554a04da9b9ab4c4f8fbe6efe
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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