Diisopropylethylamine → HCID 58154776, compound

HRID 2359394Notes

Reaction equation

HRID 2359394 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[S:13]1[CH:17]=[C:16]([C:18](O)=[O:19])[N:15]=[CH: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>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:18]([C:16]3[N:15]=[CH:14][S:13][CH:17]=3)=[O:19])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3042714-Thiazolecarboxylic acidHCID 3465192-Chloroquinolin-8-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58154776HCID 58154776, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloroquinolin-8-amine (222 mg), thiazole-4-carboxylic acid (129 mg, 1 eq), HATU (570 mg, 1.5 eq), and DIEA (246 uL, 2.0 eq) in DMF (3 mL) was stirred at room temperature overnight. The product was precipitated by the addition of water (20 mL), the product was collected by filtration and recrystallized from methanol to obtain the product as a grey solid (194 mg).

Workup

  1. customThe product was precipitated by the addition of water (20 mL)
  2. filtrationthe product was collected by filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-dc8d375efc7a4a619fbf318fad5befd5
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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